GB561571A - ª‰-(2,5-dimethoxyphenyl)-ª‰-hydroxyisopropylamine - Google Patents

ª‰-(2,5-dimethoxyphenyl)-ª‰-hydroxyisopropylamine

Info

Publication number
GB561571A
GB561571A GB16987/42A GB1698742A GB561571A GB 561571 A GB561571 A GB 561571A GB 16987/42 A GB16987/42 A GB 16987/42A GB 1698742 A GB1698742 A GB 1698742A GB 561571 A GB561571 A GB 561571A
Authority
GB
United Kingdom
Prior art keywords
stage
dimethoxyphenyl
ketoisopropylamine
isonitrosopropiophenone
dimethoxy
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
GB16987/42A
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.)
SmithKline Beecham Corp
Original Assignee
Burroughs Wellcome Co USA
Burroughs Wellcome and Co USA Inc
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 Burroughs Wellcome Co USA, Burroughs Wellcome and Co USA Inc filed Critical Burroughs Wellcome Co USA
Publication of GB561571A publication Critical patent/GB561571A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

b -(2 : 5 -dimethoxyphenyl)-b -hydroxyisopropylamine is prepared by a two-stage reduction of 2 : 5-dimethoxy-a -isonitrosopropiophenone using a palladized charcoal catalyst for the first stage and a platinum catalyst for the second stage. The first stage in the reduction results in the formation of the ketoisopropylamine. In an example, 2 : 5-dimethoxypropiophenone is treated in ether solution with methyl nitrite and hydrogen chloride to form 2 : 5-dimethoxy-a -isonitrosopropiophenone. This is dissolved in absolute alcohol containing hydrogen chloride and hydrogenated in the presence of palladized charcoal to form b -(2 : 5-dimethoxyphenyl)-b -ketoisopropylamine hydrochloride, which on further hydrogenation in aqueous solution in presence of platinum oxide gives the required b -(2 : 5-dimethoxyphenyl) - b -hydroxyisopro - pylamine. Acetylation with acetic anhydride gives the diacetyl derivative. The compounds of the present invention act as a powerful, long acting pressor and mydriatic.
GB16987/42A 1942-06-24 1942-11-30 ª‰-(2,5-dimethoxyphenyl)-ª‰-hydroxyisopropylamine Expired GB561571A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US561571XA 1942-06-24 1942-06-24

Publications (1)

Publication Number Publication Date
GB561571A true GB561571A (en) 1944-05-24

Family

ID=22002545

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16987/42A Expired GB561571A (en) 1942-06-24 1942-11-30 ª‰-(2,5-dimethoxyphenyl)-ª‰-hydroxyisopropylamine

Country Status (1)

Country Link
GB (1) GB561571A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028429A (en) * 1959-09-24 1962-04-03 Nepera Chemical Co Inc Method of producing 2-amino-1-phenyl-1-propanol hydrochloride

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028429A (en) * 1959-09-24 1962-04-03 Nepera Chemical Co Inc Method of producing 2-amino-1-phenyl-1-propanol hydrochloride

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