GB1041696A

GB1041696A – Manufacture of benzo[a]quinolizines
– Google Patents

GB1041696A – Manufacture of benzo[a]quinolizines
– Google Patents
Manufacture of benzo[a]quinolizines

Info

Publication number
GB1041696A

GB1041696A
GB23336/64A
GB2333664A
GB1041696A
GB 1041696 A
GB1041696 A
GB 1041696A
GB 23336/64 A
GB23336/64 A
GB 23336/64A
GB 2333664 A
GB2333664 A
GB 2333664A
GB 1041696 A
GB1041696 A
GB 1041696A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
group
formula
product
salt
Prior art date
1963-06-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Application number
GB23336/64A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

F Hoffmann La Roche AG

Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1963-06-07
Filing date
1964-06-05
Publication date
1966-09-07

1963-06-07
Priority claimed from CH704063A
external-priority
patent/CH450414A/en

1964-06-05
Application filed by F Hoffmann La Roche AG
filed
Critical
F Hoffmann La Roche AG

1966-09-07
Publication of GB1041696A
publication
Critical
patent/GB1041696A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

RMOYSWDTCQZJGS-UHFFFAOYSA-N
6h-benzo[a]quinolizine
Chemical class

C1=CC=CN2CC=C(C=CC=C3)C3=C21
RMOYSWDTCQZJGS-UHFFFAOYSA-N
0.000
title
1

238000004519
manufacturing process
Methods

0.000
title
1

125000004432
carbon atom
Chemical group

C*

0.000
abstract
5

125000000217
alkyl group
Chemical group

0.000
abstract
3

150000001875
compounds
Chemical class

0.000
abstract
3

239000007859
condensation product
Substances

0.000
abstract
3

239000000047
product
Substances

0.000
abstract
3

239000002253
acid
Substances

0.000
abstract
2

125000003342
alkenyl group
Chemical group

0.000
abstract
2

125000006615
aromatic heterocyclic group
Chemical group

0.000
abstract
2

150000001768
cations
Chemical class

0.000
abstract
2

150000003839
salts
Chemical class

0.000
abstract
2

DINICVDBPYYNJT-UHFFFAOYSA-N
1-methyl-1-(1,2,3,4-tetrahydroisoquinolin-1-yl)-2H-benzo[a]quinolizin-5-ium
Chemical class

C1(NCCC2=CC=CC=C12)C1(CC=C[N+]=2C=CC3=C(C1=2)C=CC=C3)C
DINICVDBPYYNJT-UHFFFAOYSA-N
0.000
abstract
1

NKSZCPBUWGZONP-UHFFFAOYSA-N
3,4-dihydroisoquinoline
Chemical class

C1=CC=C2C=NCCC2=C1
NKSZCPBUWGZONP-UHFFFAOYSA-N
0.000
abstract
1

QCRCVAMGUZYIKG-UHFFFAOYSA-N
6,7-dihydrobenzo[a]quinolizin-5-ium
Chemical class

C1=CC=C2CC[N+]3=CC=CC=C3C2=C1
QCRCVAMGUZYIKG-UHFFFAOYSA-N
0.000
abstract
1

125000003710
aryl alkyl group
Chemical group

0.000
abstract
1

XYIUTVDOILVALE-UHFFFAOYSA-N
benzo[a]quinolizin-5-ium
Chemical class

C1=CC=C2C3=CC=CC=C3C=C[N+]2=C1
XYIUTVDOILVALE-UHFFFAOYSA-N
0.000
abstract
1

238000009903
catalytic hydrogenation reaction
Methods

0.000
abstract
1

238000006243
chemical reaction
Methods

0.000
abstract
1

125000001301
ethoxy group
Chemical group

[H]C([H])([H])C([H])([H])O*

0.000
abstract
1

238000005984
hydrogenation reaction
Methods

0.000
abstract
1

AWJUIBRHMBBTKR-UHFFFAOYSA-N
isoquinoline
Chemical class

C1=NC=CC2=CC=CC=C21
AWJUIBRHMBBTKR-UHFFFAOYSA-N
0.000
abstract
1

229910052987
metal hydride
Inorganic materials

0.000
abstract
1

150000004681
metal hydrides
Chemical class

0.000
abstract
1

125000000956
methoxy group
Chemical group

[H]C([H])([H])O*

0.000
abstract
1

238000002360
preparation method
Methods

0.000
abstract
1

125000001424
substituent group
Chemical group

0.000
abstract
1

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine

C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine

C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine

C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine

C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems

C07D455/08—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems having an isoquinolyl-1, a substituted isoquinolyl-1 or an alkylenedioxyisoquinolyl-1 radical linked through only one carbon atom, attached in position 2, e.g. emetine

Abstract

The invention comprises (1) compounds of formula in which R is an alkyl group having 1-4 carbon atoms, R1, R2, R3 and R4 represent methoxy or ethoxy group, and Ra is present and represents an alkenyl group having 2-7 carbon atoms, and (2) the preparation of compounds of the formula given above in which R, R1, R2, R3, R4 are as defined above, and R is an aralkyl group in which the alkyl portion has 1-4 carbon atoms, an alkyl group having 1-7 carbon atoms or an alkenyl group having 2-7 carbon atoms, and in which the broken line denotes that the substituents attached thereby are optional, and acid addition salts thereof, which comprises condensing a 6,7-dihydro-benzo[a]quinolizinium salt having a cation of formula with a 3,4-dihydroisoquinolinium salt having a cation of formula to give a tetrahydroisoquinolinyl-methyl -dihydrobenzo[a]quinolizinium salt and either first hydrogenating the heterocyclic aromatic ring of this compound and then dearalkylating or reducing, if desired, the hydrogenated product to remove any N-aralkyl group or reduce any N-alkenyl group to an N-alkyl group, or first carrying out the dearalkylation or reduction and then hydrogenating the dearalkylation or reduction product, and in either case if desired converting the product to an acid addition salt. The reaction between the benzo[a]quinolizinium salts and isoquinolinium salts of Formulae II and III is preferably carried out in a basic medium at a temperature within the approximate range of – 10 DEG C. to + 70 DEG C. The hydrogenation of the aromatic heterocyclic ring of the condensation product is conveniently effected using a metal hydride in an aqueous or alkanolic solution. The dearalkylation of any N-aralkyl condensation product or the reduction of any N-alkenyl condensation product can conveniently be effected by catalytic hydrogenation.

GB23336/64A
1963-06-07
1964-06-05
Manufacture of benzo[a]quinolizines

Expired

GB1041696A
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

CH704063A

CH450414A
(en)

1963-06-07
1963-06-07

Process for the preparation of benzo (a) quinolizine derivatives

CH704163A

CH442316A
(en)

1963-06-07
1963-06-07

Process for the preparation of benzo (a) quinolizine derivatives

Publications (1)

Publication Number
Publication Date

GB1041696A
true

GB1041696A
(en)

1966-09-07

Family
ID=25700619
Family Applications (6)

Application Number
Title
Priority Date
Filing Date

GB45825/65A
Expired

GB1041698A
(en)

1963-06-07
1964-06-05
Novel 3,4-dihydro-isoquinolinium salts

GB23336/64A
Expired

GB1041696A
(en)

1963-06-07
1964-06-05
Manufacture of benzo[a]quinolizines

GB45824/65A
Expired

GB1041697A
(en)

1963-06-07
1964-06-05
Novel 6,7-dihydro-benzo[a]quinolizinium salts and a process for the preparation thereof

GB18814/66A
Expired

GB1041699A
(en)

1963-06-07
1964-06-05
Novel tetrahydro isoquinolinyl-methyldihydrobenzo[a]quinolizinium salts

GB23337/64A
Expired

GB1042205A
(en)

1963-06-07
1964-06-05
Manufacture of benzo[a]quinolizines

GB46933/65A
Expired

GB1042206A
(en)

1963-06-07
1964-06-05
Benzo[a]quinolizine amides and the preparation thereof

Family Applications Before (1)

Application Number
Title
Priority Date
Filing Date

GB45825/65A
Expired

GB1041698A
(en)

1963-06-07
1964-06-05
Novel 3,4-dihydro-isoquinolinium salts

Family Applications After (4)

Application Number
Title
Priority Date
Filing Date

GB45824/65A
Expired

GB1041697A
(en)

1963-06-07
1964-06-05
Novel 6,7-dihydro-benzo[a]quinolizinium salts and a process for the preparation thereof

GB18814/66A
Expired

GB1041699A
(en)

1963-06-07
1964-06-05
Novel tetrahydro isoquinolinyl-methyldihydrobenzo[a]quinolizinium salts

GB23337/64A
Expired

GB1042205A
(en)

1963-06-07
1964-06-05
Manufacture of benzo[a]quinolizines

GB46933/65A
Expired

GB1042206A
(en)

1963-06-07
1964-06-05
Benzo[a]quinolizine amides and the preparation thereof

Country Status (8)

Country
Link

US
(1)

US3359264A
(en)

BE
(2)

BE648824A
(en)

BR
(2)

BR6459690D0
(en)

CH
(1)

CH442316A
(en)

DK
(1)

DK123358B
(en)

GB
(6)

GB1041698A
(en)

NL
(2)

NL6405025A
(en)

SE
(2)

SE326448B
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

USD435684S
(en)

2000-02-08
2000-12-26
Gary Products Group, Inc.
Tube light surface clip

Families Citing this family (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB1059326A
(en)

*

1962-10-31
1967-02-15
Glaxo Lab Ltd
Reactions and intermediates of use in syntheses of compounds of the 2-dehydroemetine series

US4133812A
(en)

*

1975-11-21
1979-01-09
Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.
Process for producing benzo (a) quinolizine derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3159638A
(en)

*

1964-12-01

Xcha-chj

US3105835A
(en)

*

1963-10-01

Isoquinoline derivatives

US3240782A
(en)

*

1966-03-15

Method of converting z-dehydro-isoeme
tine into z-dehydro-emetine and inter-
mediates therein

GB977789A
(en)

*

1960-12-02
1964-12-16
Glaxo Group Ltd
Emetine derivatives and their preparation

1963

1963-06-07
CH
CH704163A
patent/CH442316A/en
unknown

1964

1964-05-06
NL
NL6405025A
patent/NL6405025A/xx
unknown

1964-05-11
SE
SE05726/64A
patent/SE326448B/xx
unknown

1964-05-21
NL
NL6405645A
patent/NL125065C/xx
active

1964-06-03
SE
SE6717/64A
patent/SE315284B/xx
unknown

1964-06-03
BR
BR159690/64A
patent/BR6459690D0/en
unknown

1964-06-03
BR
BR159689/64A
patent/BR6459689D0/en
unknown

1964-06-04
BE
BE648824D
patent/BE648824A/xx
unknown

1964-06-04
BE
BE648823D
patent/BE648823A/fr
unknown

1964-06-05
GB
GB45825/65A
patent/GB1041698A/en
not_active
Expired

1964-06-05
GB
GB23336/64A
patent/GB1041696A/en
not_active
Expired

1964-06-05
GB
GB45824/65A
patent/GB1041697A/en
not_active
Expired

1964-06-05
GB
GB18814/66A
patent/GB1041699A/en
not_active
Expired

1964-06-05
US
US373043A
patent/US3359264A/en
not_active
Expired – Lifetime

1964-06-05
GB
GB23337/64A
patent/GB1042205A/en
not_active
Expired

1964-06-05
GB
GB46933/65A
patent/GB1042206A/en
not_active
Expired

1964-06-08
DK
DK285364AA
patent/DK123358B/en
unknown

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

USD435684S
(en)

2000-02-08
2000-12-26
Gary Products Group, Inc.
Tube light surface clip

Also Published As

Publication number
Publication date

SE315284B
(en)

1969-09-29

BR6459689D0
(en)

1973-08-02

US3359264A
(en)

1967-12-19

BE648824A
(en)

1964-12-04

SE326448B
(en)

1970-07-27

BE648823A
(en)

1964-12-04

GB1042206A
(en)

1966-09-14

GB1042205A
(en)

1966-09-14

GB1041699A
(en)

1966-09-07

BR6459690D0
(en)

1973-08-02

DE1445895A1
(en)

1969-11-27

NL6405645A
(en)

1964-12-08

NL125065C
(en)

1968-04-16

GB1041697A
(en)

1966-09-07

GB1041698A
(en)

1966-09-07

DK123358B
(en)

1972-06-12

CH442316A
(en)

1967-08-31

NL6405025A
(en)

1964-12-08

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