GB683978A - Improvements in and relating to the preparation of substituted tertiary amino carbinols - Google Patents

Improvements in and relating to the preparation of substituted tertiary amino carbinols

Info

Publication number
GB683978A
GB683978A GB1794950A GB1794950A GB683978A GB 683978 A GB683978 A GB 683978A GB 1794950 A GB1794950 A GB 1794950A GB 1794950 A GB1794950 A GB 1794950A GB 683978 A GB683978 A GB 683978A
Authority
GB
United Kingdom
Prior art keywords
bromo
preparation
alcohols
diphenylhexanol
thienyl
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
GB1794950A
Inventor
Paul Anthony Barrett
Samuel Wilkinson
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB1794950A priority Critical patent/GB683978A/en
Publication of GB683978A publication Critical patent/GB683978A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

Landscapes

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

Abstract

Amino-alcohols of the formula <FORM:0683978/IV (b)/1> where n is 3-8 and R1 and R2 are the same or different alkyl radicals of 1-4 carbon atoms or else NR1R2 is a morpholino, pyrrolidino or piperidino group, are prepared by treating the corresponding chloro- or bromo-alcohols with HNR1R2. Examples describe the preparation of amino-alcohols where n is 3, 4, 5 and 8 and NR1R2 is dimethylamino, diethylamino, morpholino, pyrrolidino and piperidino. They form salts, e.g. hydrochlorides and oxalates. Specifications 682,160 and 682,161 describe different methods of making the amino-alcohols. Halo-alcohols of the formula <FORM:0683978/IV (b)/2> are made by treating halo-esters Hal.(CH2)n. COOR with a thienyl-magnesium halide or thienyl-lithium compound and hydrolysing the resultant complex. Examples describe the preparation of 5 - bromo - 1 : 1 - di - 21 - thienyl-pentanol, 4 - chloro - 1 : 1 - di - 21 - thienylbutanol, 6 - bromo - 1 : 1 - di - 21 - thienylhexanol and 9-bromo-1 : 1-di-21-thienylnonanol. The Provisional Specification describes the preparation of aminoalcohols <FORM:0683978/IV (b)/3> where R1 and R2 are identical aryl or thienyl radicals (which may be substituted), n is 3-11 and R3 and R4 are alkyl or form a morpholine, pyrrolidine or piperidine ring. These are made by reacting chloro-, bromo- or iodo-esters Hal-(CH2)n-COOR with organometallic compounds to give halocarbinols R1R2C(OH)-(CH2)n-Hal and treating the latter with the appropriate secondary amine. Examples show the preparation of 6-bromo-1 : 1-diphenylhexanol, 6 - piperidino - 1 : 1 - diphenylhexanol, 6-pyrrolidino - 1 : 1 - diphenylhexanol and 6 - morpholino-1 : 1-diphenylhexanol.
GB1794950A 1949-07-18 1949-07-18 Improvements in and relating to the preparation of substituted tertiary amino carbinols Expired GB683978A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1794950A GB683978A (en) 1949-07-18 1949-07-18 Improvements in and relating to the preparation of substituted tertiary amino carbinols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1794950A GB683978A (en) 1949-07-18 1949-07-18 Improvements in and relating to the preparation of substituted tertiary amino carbinols

Publications (1)

Publication Number Publication Date
GB683978A true GB683978A (en) 1952-12-10

Family

ID=10104062

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1794950A Expired GB683978A (en) 1949-07-18 1949-07-18 Improvements in and relating to the preparation of substituted tertiary amino carbinols

Country Status (1)

Country Link
GB (1) GB683978A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2377397A1 (en) * 1977-01-12 1978-08-11 Degussa PROCESS FOR THE PREPARATION OF (1,1-DITHIENYL- (3) -1-HYDROXYPROPYL- (3)) - (1-PHENYL-1-HYDROXYPROPYL- (2)) - AMINE AND (1,1-DITHIENYL- ( 3) -PROPEN- (1) -YL- (3)) - (1-PHENYL-PROPYL- (2)) - AMINE
EP0046337A2 (en) * 1980-08-20 1982-02-24 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2377397A1 (en) * 1977-01-12 1978-08-11 Degussa PROCESS FOR THE PREPARATION OF (1,1-DITHIENYL- (3) -1-HYDROXYPROPYL- (3)) - (1-PHENYL-1-HYDROXYPROPYL- (2)) - AMINE AND (1,1-DITHIENYL- ( 3) -PROPEN- (1) -YL- (3)) - (1-PHENYL-PROPYL- (2)) - AMINE
EP0046337A2 (en) * 1980-08-20 1982-02-24 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them
EP0046337A3 (en) * 1980-08-20 1982-09-15 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them

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