GB682160A - Improvements in and relating to the preparation of substituted aminoalcohols, alkenylamines, aminoalkanes and quaternary salts thereof - Google Patents

Improvements in and relating to the preparation of substituted aminoalcohols, alkenylamines, aminoalkanes and quaternary salts thereof

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Publication number
GB682160A
GB682160A GB2711948A GB2711948A GB682160A GB 682160 A GB682160 A GB 682160A GB 2711948 A GB2711948 A GB 2711948A GB 2711948 A GB2711948 A GB 2711948A GB 682160 A GB682160 A GB 682160A
Authority
GB
United Kingdom
Prior art keywords
piperidino
phenyl
thienyl
pyrrolidino
hexan
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
GB2711948A
Inventor
Paul Anthony Barrett
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 GB2711948A priority Critical patent/GB682160A/en
Priority to FR997728D priority patent/FR997728A/en
Publication of GB682160A publication Critical patent/GB682160A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • 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

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

Abstract

682,160. Substituted #-(tertiary amino)- alcohols, alkanes and alkenes and their quaternary salts. WELLCOME FOUNDATION, Ltd. Oct. 18, 1949 [Oct. 18, 1948], No. 27119/48. Class 2 (iii). A process for the production of substituted #(tertiary aminoalkyl)-carbinols of the formula wherein R 1 and R 2 are alike or different and are alkyl, aralkyl, thienyl or pyridyl groups, or aryl groups optionally substituted by alkyl or alkoxy groups containing up to 4 carbon atoms or by halogen atoms, R 3 and R 4 are alkyl, alkenyl, cycloalkyl, or aralkyl groups or R 3 and R. together with the adjacent nitrogen atom constitute a morpholino, pyrrolidino, piperidino N<SP>1</SP>-alkyl-N-piperazino group and -(CH 2 ) n - is a straight chain which may carry alkyl substituents, n being an integer from 4 to 10, comprises reacting an ester of the formula or a salt thereof with an organo lithium compound of the formula R 1 Li or R 2 Li or a ketone of the formula or a salt thereof with an organo lithium compound of the formula R 2 Li where R is an alkyl group, and R 1 , R 2' R 3 , R 4 and n have the above meanings (except that R 1 may not be pyridyl) and hydrolysing the organo-metallic compound so formed. Ketones of formula III used in preforming the carbinols where R 1 and R 2 are unlike, are described in Specification 682,161. The carbinols I obtained are converted to the corresponding alkenes or where R 1 is alkyl or aralkyl, to an isomer with the double bond in a different position, by treatment with a dehydrating agent, e.g. mineral acids, carboxylic acid chlorides or anhydrides, or (where R 1 or R 2 are pyridyl or benzyl), thionyl chloride. The aminoalkanes (IV) are converted to the corresponding aminoalkanes R 1 R 2 CH(CH 2 ) n NR 3 R 3 in which R 1 , R 2 , R 3 , R 4 and n have the above meanings (except that R 1 or R 2 may not be thienyl and R 3 or R 4 may not be alkenyl) by reduction of the alkanes (IV) (in which R 1 and R 2 may not be thienyl). Corresponding quaternary ammonium salts of the amino-alcohols, alkanes or alkenes, are formed by reaction with an alkyl or aralkyl ester or salt R,X in which X is an acid radical, e.g. chloride, bromide, iodide or methosulphate radical. Examples describe the preparation of (1) 1 : 1-diphenyl-6-(1<SP>1</SP>-piperidino) hexan-1-ol, its hydrochloride and methiodide, from 5-N-piperidino amyl phenyl ketone and lithium phenyl; (2) 1 : 1-diphenyl-5- diethylaminopentan-1-ol, its hydrochloride and its methiodide, from 4-diethylaminovaleric acid ethyl ester and lithium phenyl. Similarly to (1) are prepared (10) 11-N-piperidino-1 : 1-diphenylundecan-1-ol and its oxalate; (12) 1-N- piperidino-6-phenyloctan-6-ol and its oxalate; (13) 1 - N - piperidino - 6 - ethyldecan - 6 - ol; (16) 7 - N - pyrrolidino - 1 : 2 - diphenylheptan - 2 - ol; (17) 1 - N - pyrrolidino - 6- phenyl - 6 - p - - tolylhexan - 6 - ol ; (18) 1 - N- pyrrolidyl - 6 - phenyl - 6 - p - methoxyphenylhexan - 6 - ol ; (19) 6 - N - methyl - N - benzyl 1 : 1 - diphenyl hexan - 1 - ol ; (20) 6 - N- morpholino - 1 : 1 - diphenylhexan - 1 - ol ; (21) 6 - N - piperidino - 1 - (21 - thienyl) - 1- phenylhexan - 1 - ol ; (22) 6 - N - piperidino- 1 (21 - pyridyl) - 1 - phenylhexan - 1 - ol; (23) 6 - diallylamino - 1 : 1 - diphenylhexan - 1 - ol; (25) 6 - N - morpholino - 1 - phenyl - 1 - (2<SP>1</SP>- thienyl) hexan - 1 - ol (26) 6 - N - pyrrolidino - 1 - phenyl - 1 - (2<SP>1</SP> - thienyl) - hexan - 1- ol; (27) 5 - N - piperidino - 1 - phenyl - 1 - (2<SP>1</SP>- thienyl) - pentan - 1 - ol and its oxalate; (28) 9 - N - piperidino - 1 - phenyl - 1 - (21 - thienyl)- nonan - 1 - ol; (29) 9 - N - - pyrrolidino - 1- phenyl 1 - (2<SP>1</SP> - thienyl) - nonan - 1 - ol; (30) 11 - N - piperidino - 1 - phenyl - 1 - (21 - thienyl)- undecan - 1 - ol; (32) 9 - N - pyrrolidino - 1- phenyl - 1 (21 - pyridyl) - nonan - 1 - ol; (33) 6 - dicyclohexylamino - 1 : 1 - diphenylhexan- 1 - ol; (34) 5 - dimethylamino - 1 - (21 - pyridyl)- 1 - phenyl - pentan - 1 - ol; (35) 5 - N - pyrrolidino - 1 - (21 - pyridyl) - 1 - phenylpentan - 1- ol; (39) 6 - N - piperidino - 1 - phenyl - 1 - pchlorophenylhexan - 1 - ol; (40) 6 - Nl - methyl- N - piperazino - 1 - phenyl - 1 - (2<SP>1</SP> - thienyl) hexan - 1 - ol; (40) 6 - butylamino - 1 - phenyl- 1 - (2<SP>1</SP> - thienyl) hexan - 1 - ol. Similarly to (2) are prepared (3) 1 : 1-diphenyl-6-diethylaminohexan-1-ol; (4) 1 : 1-diphenyl-7-N-piperidinoheptan - 1 - ol; (5) 1 : 1 - diphenyl - 7 - diethylaminoheptan - 1 - ol; (9) 9 - piperidino- 1 : 1 - diphenylnonan - 1 - ol; (11) 11 - (1<SP>1</SP>- pyrrolidino) 1 : 1 - diphenylundecan - 1 - ol; (14) 6 - N - pyrrolidino - 1 : 1 - diphenylhexan - 1 - ol; (15) 6 - butylamino - 1 : 1 - diphenylhexan - 1 - ol; (24) 9 - N - pyrrolidino- 1 : 1 - diphenylnonan - 1 - ol; (31) 5 - N - pyrrolidino - 1 : 1 - di - (2<SP>1</SP> - thienyl) - pentan - 1- ol; (36) 9 - N - piperidino - 1 : 1 - di - (21- thienyl) - nonan - 1 - ol; (37) 5 - dimethylamino- 1 : 1 - diphenylpentan - 1 - ol; (38) 6 - Nlmethyl - N - piperazino - 1 : 1 - diphenylhexan- 1 - ol; (42) 6 - dimethylamino - 1 : 1 - di -(2<SP>1</SP>- pyridyl) - hexan - 1 - ol; (43) 5 - N - pyrrolidino- 1 : 1 - di - (2<SP>1</SP> - pyridyl) - hexan - 1 - ol; (44) 5 - dimethylamino - 1 : 1 - di - (2<SP>1</SP> - thienyl)- hexan-1-ol. In example (6) 5-N-piperidino- 1 : 1 - diphenylpent - 1 - ene is prepared by dehydrating 1 : 1 - diphenyl - 5 - (1<SP>1</SP> - piperidino) - pentan - 1 - ol and converted to salts and quaternary ammonium compounds. Similarly prepared are (7) 6-diethylamino-1 :1- diphenylhex-1-ene; (8) 7-N-piperidino-1 :.1- diphenyl-hept-1-ene, its salts and its quaternary ammonium compounds. A list of further alkenes is given of formula IV, where R 1 is phenyl or ethyl, R 2 is phenyl, butyl, benzyl, ptolyl, p-anisyl or 2-thienyl, n is 4 to 10 and -NR 3 R 4 is a piperidino, pyrrolidino, dibutylamino, morpholino, N-methyl-N-benzylamino- or a dicyclohexylamino radical, and their oxalates, hydrochlorides and hydrobromides. Such alkenes are hydrogenated (examples 64 to 66) giving aminoalkanes of the above formula where R 1 and R 2 are phenyl, n is 8 or 10, -NR 3 R 4 is a piperidino or pyrrolidion radical, and their oxalates. Reference is made to Specification 646,198 as open to inspection under Sect. 91.
GB2711948A 1948-10-18 1948-10-18 Improvements in and relating to the preparation of substituted aminoalcohols, alkenylamines, aminoalkanes and quaternary salts thereof Expired GB682160A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2711948A GB682160A (en) 1948-10-18 1948-10-18 Improvements in and relating to the preparation of substituted aminoalcohols, alkenylamines, aminoalkanes and quaternary salts thereof
FR997728D FR997728A (en) 1948-10-18 1949-10-19 Substituted amino alcohols, derivatives of these alcohols and processes for the preparation of these substances

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2711948A GB682160A (en) 1948-10-18 1948-10-18 Improvements in and relating to the preparation of substituted aminoalcohols, alkenylamines, aminoalkanes and quaternary salts thereof

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GB682160A true GB682160A (en) 1952-11-05

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2824111A (en) * 1952-11-12 1958-02-18 Upjohn Co Pyrrolidines
US3128278A (en) * 1964-04-07 Substituted l
DE1183090B (en) * 1958-01-31 1964-12-10 Colgate Palmolive Co Process for the preparation of 1,4-disubstituted piperazines and their hydrochlorides
US4468522A (en) * 1981-04-10 1984-08-28 Anic S.P.A. Process for the preparation of (omega-carboalkoxy-nor.alkyl)-dialkylamines
US4894221A (en) * 1981-03-19 1990-01-16 Ab Ferrosan Method of treating plaque using morpholine compounds
JP2014505662A (en) * 2010-11-23 2014-03-06 ファエス・ファルマ・ソシエダッド・アノニマ Diphenyl-amine derivatives: uses, synthetic methods and pharmaceutical compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2931833A (en) * 1954-12-29 1960-04-05 Armour & Co Benzyldialkyl-2-(1-hydroxy-alkyl) alkyl ammonium chloride compounds

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3128278A (en) * 1964-04-07 Substituted l
US2824111A (en) * 1952-11-12 1958-02-18 Upjohn Co Pyrrolidines
DE1183090B (en) * 1958-01-31 1964-12-10 Colgate Palmolive Co Process for the preparation of 1,4-disubstituted piperazines and their hydrochlorides
US4894221A (en) * 1981-03-19 1990-01-16 Ab Ferrosan Method of treating plaque using morpholine compounds
US4468522A (en) * 1981-04-10 1984-08-28 Anic S.P.A. Process for the preparation of (omega-carboalkoxy-nor.alkyl)-dialkylamines
JP2014505662A (en) * 2010-11-23 2014-03-06 ファエス・ファルマ・ソシエダッド・アノニマ Diphenyl-amine derivatives: uses, synthetic methods and pharmaceutical compositions

Also Published As

Publication number Publication date
FR997728A (en) 1952-01-09

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