GB685750A - Improvements in or relating to isoquinoline derivatives - Google Patents

Improvements in or relating to isoquinoline derivatives

Info

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
Application number
GB1157852A
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.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Priority to GB1157852A priority Critical patent/GB685750A/en
Publication of GB685750A publication Critical patent/GB685750A/en
Expired legal-status Critical Current

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.
GB1157852A 1949-10-14 1949-10-14 Improvements in or relating to isoquinoline derivatives Expired GB685750A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (3)

* Cited by examiner, † Cited by third party
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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