GB1145255A - Tetrahydroisoquinolinium salts - Google Patents

Tetrahydroisoquinolinium salts

Info

Publication number
GB1145255A
GB1145255A GB5300066A GB5300066A GB1145255A GB 1145255 A GB1145255 A GB 1145255A GB 5300066 A GB5300066 A GB 5300066A GB 5300066 A GB5300066 A GB 5300066A GB 1145255 A GB1145255 A GB 1145255A
Authority
GB
United Kingdom
Prior art keywords
formula
reaction
dimethoxy
group
tetrahydroisoquinoline
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
GB5300066A
Inventor
Thomas Alfred Montzka
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.)
Bristol Myers Co
Original Assignee
Bristol Myers Co
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 Bristol Myers Co filed Critical Bristol Myers Co
Publication of GB1145255A publication Critical patent/GB1145255A/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
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • 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
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,145,255. Tetrahydroisoquinolinium salts. BRISTOL-MYERS CO. 18 March, 1966, No. 53000/68. Divided out of 1,145,254. Heading C2C. Compounds of the formula wherein Z# is one equivalent of an anion incapable of further reaction with the cation are prepared by reacting an alcohol of the formula with a compound capable of replacing the OH group with a group Z#, as defined, and treating this reaction product with an alkali to effect cyclization. The following synthesis is given: 6,7 - Dimethoxy - 1,2,3,4 - tetrahydroisoquinoline- 1-acetic acid ethyl ester oxalate is made by reaction of diethyl ethoxymethylenemalonate and homoveratrylamine, which product is in turn 2- methylated and converted to the hydrochloride using formaldehyde/formic acid followed by HCl. This is reduced to 6,7 Dimethoxy-1-(#- hydroxy)ethyl - 2 - methyl - 1,2,3,4 - tetrahydroisoquinoline hydrochloride, using LiAlH 4 , and finally cyclized with Na 2 CO 3 to the compound of the first formula given above, wherein Z# is p-bromobenzenesulphonate.
GB5300066A 1965-03-18 1966-03-18 Tetrahydroisoquinolinium salts Expired GB1145255A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US44092865A 1965-03-18 1965-03-18

Publications (1)

Publication Number Publication Date
GB1145255A true GB1145255A (en) 1969-03-12

Family

ID=23750774

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5300066A Expired GB1145255A (en) 1965-03-18 1966-03-18 Tetrahydroisoquinolinium salts

Country Status (1)

Country Link
GB (1) GB1145255A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3439157A1 (en) * 1983-10-25 1985-05-02 Richter Gedeon Vegyészeti Gyár R.T., Budapest 2H-AZETO (2,1-A) ISOCHINOLINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THEM
AT387778B (en) * 1983-10-25 1989-03-10 Richter Gedeon Vegyeszet METHOD FOR PRODUCING NEW 2H-AZETO (2,1-A) ISOCHINOLINE DERIVATIVES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3439157A1 (en) * 1983-10-25 1985-05-02 Richter Gedeon Vegyészeti Gyár R.T., Budapest 2H-AZETO (2,1-A) ISOCHINOLINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THEM
AT387778B (en) * 1983-10-25 1989-03-10 Richter Gedeon Vegyeszet METHOD FOR PRODUCING NEW 2H-AZETO (2,1-A) ISOCHINOLINE DERIVATIVES

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