GB430108A - Improvements relating to the preparation of histamine and its derivatives - Google Patents

Improvements relating to the preparation of histamine and its derivatives

Info

Publication number
GB430108A
GB430108A GB603834A GB603834A GB430108A GB 430108 A GB430108 A GB 430108A GB 603834 A GB603834 A GB 603834A GB 603834 A GB603834 A GB 603834A GB 430108 A GB430108 A GB 430108A
Authority
GB
United Kingdom
Prior art keywords
yield
hydrochloride
hydroxyethylglyoxaline
salt
product
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
GB603834A
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.)
Boots Pure Drug Co Ltd
Original Assignee
Boots Pure Drug Co Ltd
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 Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Priority to GB603834A priority Critical patent/GB430108A/en
Publication of GB430108A publication Critical patent/GB430108A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Histamine (4(5)-b -aminoethylglyoxaline) and its derivatives substituted by one or two alkyl groups on the nitrogen atom of the amino group, and quaternary ammonium salts derived from such N-dialkylhistamines, are prepared from 4(5)-b -hydroxyethylglyoxaline by reacting this with thionyl chloride to yield 4(5)-b -chlorethylglyoxaline hydrochloride, and reacting the latter with ammonia or an alkyl amine. When a primary alkyl amine is used, it may be taken in the form of its p-toluenesulphonyl derivative, in which event the reaction product is saponified to remove the p-toluenesulphonyl group. Examples are given in which 4(5)-b -chlorethylglyoxaline hydrochloride is reacted with (1) methylamine, (2) p-toluenesulphomethylamide, (3) ammonia, (4) trimethylamine, (5) dimethylamine and (6) ethylamine; example 1 gives details of the recovery of the base as its dipicrate, and the conversion of the latter into the dihydrochloride; in example 2, the reaction product is hydrolyzed with dilute sulphuric acid to remove the p-toluenesulphonyl group, the final product being identical with that of example 1 (4(5)-b -methylaminoethylglyoxaline hydrochloride); the product of example 4 is a quaternary ammonium salt (4(5)-b -trimethylaminoethylglyoxaline chloride hydrochloride). 4(5)-b -Hydroxyethylglyoxaline is obtainable as follows. A salt of a -aminobutyrolactone is reduced with sodium amalgam to yield a salt of a -amino-g -hydroxybutyraldehyde; the latter reacts with ammonium thiocyanate to yield 2-thiol-4(5) - b - hydroxyethylglyoxaline, from which 4(5)-b -hydroxyethylglyoxaline is obtainable by oxidation with dilute nitric acid. The Provisional Specification refers to an alternative method in which ethyl g -phenoxy-a -aminobutyrate hydrochloride is reduced with sodium amalgam to yield g -phenoxy-a -aminobutyraldehyde, which is reacted with ammonium thiocyanate to form 2-thiol-4(5)-b -phenoxyethylglyoxaline; the latter is oxidized to yield 4(5)-b -phenoxyethylglyoxaline, from which the required product is obtained by dearylation.
GB603834A 1934-02-23 1934-02-23 Improvements relating to the preparation of histamine and its derivatives Expired GB430108A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB603834A GB430108A (en) 1934-02-23 1934-02-23 Improvements relating to the preparation of histamine and its derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB603834A GB430108A (en) 1934-02-23 1934-02-23 Improvements relating to the preparation of histamine and its derivatives

Publications (1)

Publication Number Publication Date
GB430108A true GB430108A (en) 1935-06-13

Family

ID=9807293

Family Applications (1)

Application Number Title Priority Date Filing Date
GB603834A Expired GB430108A (en) 1934-02-23 1934-02-23 Improvements relating to the preparation of histamine and its derivatives

Country Status (1)

Country Link
GB (1) GB430108A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2677692A (en) * 1954-05-04 Imidazole compounds
US6403806B1 (en) * 1998-12-23 2002-06-11 Maxim Pharmaceuticals, Inc. Synthesis of histamine dihydrochloride

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2677692A (en) * 1954-05-04 Imidazole compounds
US6403806B1 (en) * 1998-12-23 2002-06-11 Maxim Pharmaceuticals, Inc. Synthesis of histamine dihydrochloride
US6528654B2 (en) 1998-12-23 2003-03-04 Maxim Pharmaceuticals, Inc. Synthesis of histamine dihydrochloride
US6620942B2 (en) 1998-12-23 2003-09-16 Maxim Pharmaceuticals Synthesis of histamine dihydrochloride

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