GB1024650A - Benzofuran derivatives and process for their production - Google Patents

Benzofuran derivatives and process for their production

Info

Publication number
GB1024650A
GB1024650A GB37536/62A GB3753662A GB1024650A GB 1024650 A GB1024650 A GB 1024650A GB 37536/62 A GB37536/62 A GB 37536/62A GB 3753662 A GB3753662 A GB 3753662A GB 1024650 A GB1024650 A GB 1024650A
Authority
GB
United Kingdom
Prior art keywords
benzofuran
beta
carbon atoms
carboxylic acid
atoms inclusive
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
GB37536/62A
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.)
Takeda GmbH
Original Assignee
Byk Gulden Lomberg Chemische Fabrik GmbH
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
Priority claimed from DEB64656A external-priority patent/DE1203276B/en
Application filed by Byk Gulden Lomberg Chemische Fabrik GmbH filed Critical Byk Gulden Lomberg Chemische Fabrik GmbH
Publication of GB1024650A publication Critical patent/GB1024650A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)

Abstract

The invention comprises 3-(beta-aminoethyl)-benzofurans, or a hydrochloride thereof, having the general formula <FORM:1024650/C2/1> wherein R1 is hydrogen, hydroxy, methoxy, or benzyloxy, R2 is lower alkyl having 1-5 carbon atoms inclusive, and R3 is hydrogen, carbethoxy or an acyl group derived from an aliphatic or aromatic carboxylic acid which is optionally substituted by amino, halogen or a lower alkoxy having 1-5 carbon atoms inclusive, said aliphatic derivative containing 1-5 carbon atoms inclusive, and a process for the preparation thereof which comprises converting a compound having a general formula <FORM:1024650/C2/2> or a C1 to C5 alkyl ester or acid chloride thereof, wherein R1 and R2 have the same significance as stated above, into the corresponding 3-carboxylic acid dimethylamide, reducing the latter with an alkali metal aluminium hydride to the corresponding 3 - dimethylaminomethyl benzofuran, preparing a quaternary ammonium salt therefrom, reacting the quaternary ammonium salt with metal cyanide to form the corresponding 3-cyanomethyl benzofuran, reducing the latter, or optionally a corresponding 3-carbonamidemethyl benzofuran derived therefrom by partial hydrolysis, with an alkyl metal aluminium hydride and either (a) converting the resultant corresponding 3-(beta-amino-ethyl) benzofuran into a hydrochloride, (b) reacting the resultant corresponding 3-(beta-aminoethyl) benzofuran with an optionally substituted aliphatic carboxylic acid having up to 5 carbon atoms inclusive or their C1 to C5 alkyl esters, or with an optionally substituted aromatic carboxylic acid to form the corresponding 3-(beta-acylaminoethyl) benzofuran, or (c) reacting the resultant corresponding 3-(beta-aminoethyl) benzofuran with ethyl chloroformate to form a compound of the formula 2 wherein R3 is carbethoxy. The benzyl group of a benzyloxy in a position corresponding R1 in formulae 1 and 2 in an intermediate or product of the product of the invention may be removed by reduction with palladium/hydrogen or other suitable reducing agent in a suitable organic solvent to yield intermediates and final products wherein the R1 group is a 3-hydroxy.
GB37536/62A 1961-11-03 1962-10-04 Benzofuran derivatives and process for their production Expired GB1024650A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB64656A DE1203276B (en) 1961-11-03 1961-11-03 Process for the preparation of N-substituted 3- (beta-aminoaethyl) -coumarones

Publications (1)

Publication Number Publication Date
GB1024650A true GB1024650A (en) 1966-03-30

Family

ID=6974465

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37536/62A Expired GB1024650A (en) 1961-11-03 1962-10-04 Benzofuran derivatives and process for their production

Country Status (1)

Country Link
GB (1) GB1024650A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5130334A (en) * 1987-03-25 1992-07-14 Pfizer Inc. Indane sulfonamide anti-arrhythmic agents

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5130334A (en) * 1987-03-25 1992-07-14 Pfizer Inc. Indane sulfonamide anti-arrhythmic agents

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