GB685750A - Improvements in or relating to isoquinoline derivatives - Google Patents
Improvements in or relating to isoquinoline derivativesInfo
- Publication number
- GB685750A GB685750A GB1157852A GB1157852A GB685750A GB 685750 A GB685750 A GB 685750A GB 1157852 A GB1157852 A GB 1157852A GB 1157852 A GB1157852 A GB 1157852A GB 685750 A GB685750 A GB 685750A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- compound
- obtainable
- reduction
- prepared
- Prior art date
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1 - Benzyl - 3 - methyl - 1 : 2 : 3 : 4 : 5 : 6 : 7 : 8 - octahydroisoquinolines of the general formula <FORM:0685750/IV (b)/1> (wherein R11 and R111 are the same or different and each represent hydrogen or a methoxy group), and their hydrohalides, are manufactured by (a) catalytic hydrogenation, if desired in the presence of caustic alkali, of quaternary compounds of the general formula <FORM:0685750/IV (b)/2> (obtainable by the process of Specification 685,748) or (in the case of the free bases) by (b) methylation of a compound of the general formula <FORM:0685750/IV (b)/3> (obtainable by the process of Specification 685,749) by reaction with formaldehyde followed by reduction, or (c) reduction with lithium aluminium hydride of a compound of the general formula <FORM:0685750/IV (b)/4> (obtainable by reacting a compound of the general formula (C) with ethyl formate). In examples: (1) 1-benzyl-3 : 4 : 5 : 6 : 7 : 8-hexahydroisoquinoline is prepared and converted to its methobromide as described in example (1) of Specification 685,748 and the quaternary compound is hydrogenated in methanolic caustic potash in the presence of Raney nickel; (2) 1-(p-methoxybenzyl) - 1 : 2 : 3 : 4 : 5 : 6 : 7 : 8 - octahydroisoquinoline is prepared as described in example (1) of Specification 685,749 and is reacted with aqueous formaldehyde in methanol followed by hydrogenation in the presence of Raney nickel or reduction with formic acid; (3) 1 - (31 : 41 - dimethoxybenzyl) - 1 : 2 : 3 : 4 : 5 : : 7 : 8-octahydroisoquinoline is prepared as described in example (2) of Specification 685,749 and is reacted with formaldehyde followed by hydrogenation as in (2), or is heated with ethyl formate and the N-formyl compound reduced with lithium aluminium hydride. Specification 685,747 also is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1157852A GB685750A (en) | 1949-10-14 | 1949-10-14 | Improvements in or relating to isoquinoline derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1157852A GB685750A (en) | 1949-10-14 | 1949-10-14 | Improvements in or relating to isoquinoline derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB685750A true GB685750A (en) | 1953-01-07 |
Family
ID=9988816
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1157852A Expired GB685750A (en) | 1949-10-14 | 1949-10-14 | Improvements in or relating to isoquinoline derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB685750A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0315886A2 (en) * | 1987-11-11 | 1989-05-17 | F. Hoffmann-La Roche Ag | Isoquinoline derivatives, their manufacture and use |
CN103058928A (en) * | 2013-01-29 | 2013-04-24 | 苏州立新制药有限公司 | Preparation method of dextromethorphan intermediate 1-(4-methoxyl) benzyl-1,2,3,4,5,6,7,8-octahydro isoquinoline |
-
1949
- 1949-10-14 GB GB1157852A patent/GB685750A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0315886A2 (en) * | 1987-11-11 | 1989-05-17 | F. Hoffmann-La Roche Ag | Isoquinoline derivatives, their manufacture and use |
EP0315886A3 (en) * | 1987-11-11 | 1990-04-25 | F. Hoffmann-La Roche Ag | Isoquinoline derivatives, their manufacture and use |
CN103058928A (en) * | 2013-01-29 | 2013-04-24 | 苏州立新制药有限公司 | Preparation method of dextromethorphan intermediate 1-(4-methoxyl) benzyl-1,2,3,4,5,6,7,8-octahydro isoquinoline |
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