GB789033A - Improvements in or relating to substituted aralkyl-phenyl-alkylamines - Google Patents

Improvements in or relating to substituted aralkyl-phenyl-alkylamines

Info

Publication number
GB789033A
GB789033A GB30015/55A GB3001555A GB789033A GB 789033 A GB789033 A GB 789033A GB 30015/55 A GB30015/55 A GB 30015/55A GB 3001555 A GB3001555 A GB 3001555A GB 789033 A GB789033 A GB 789033A
Authority
GB
United Kingdom
Prior art keywords
ethylamino
methyl
ethan
methoxyphenyl
hydrochloride
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
GB30015/55A
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.)
Koninklijke Philips NV
Original Assignee
Philips Gloeilampenfabrieken NV
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 Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of GB789033A publication Critical patent/GB789033A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom

Abstract

The invention comprises compounds of the formula <FORM:0789033/IV (b)/1> (wherein R is a divalent alkylene group of 2-5 carbon atoms and Y1 and Y2 are either each OH or one of them is H and the other OH) and acid-addition salts thereof, and their preparation by reduction of ketones of the formula <FORM:0789033/IV (b)/2> or acid-addition salts thereof (wherein R1O is OH or esterified or etherified OH capable of being converted into OH by saponification with dilute acids or alkalis or of being de-etherified by catalytic hydrogenation or by treatment with strong inorganic acids, and Y11 and Y21 are as Y1 and Y2 or, when OH, are similarly protected) with saponification or de-etherification when necessary. When the aromatic OH groups are protected by etherification with benzyl alcohol or diphenyl or triphenyl methanol then they may be converted into free OH groups in the same reaction step as that in which the keto group is reduced, by hydrogenation in the presence of a noble metal catalyst, e.g. finely-divided palladium on carbon, barium sulphate or calcium carbonate. In an alternative procedure in which OR1 is a benzyloxy or a diphenylmethoxy or triphenylmethoxy group and Y11 and/or Y21 is or are OH etherified by a lower aliphatic alcohol, e.g. methanol, the group R1O is de-etherified by catalytic hydrogenation without substantial reduction of the keto group, Y11 and/or Y21\h is or are then de-etherified with a strong inorganic acid, e.g. HBr or HI, and, finally, the keto group is reduced by hydrogenation in presence of a noble metal. In a further modification in which R1O, Y11 and/or Y21 are hydroxyl groups etherified with a lower aliphatic alcohol these groups are de-alkylated with a strong inorganic acid prior to reduction of the keto group as before. Other conventional reducing methods are also referred to. Reference is also made to the preparation of the compounds of the invention by reacting a compound of the general formula <FORM:0789033/IV (b)/3> (R1O being OH or an ether group) with a compound of the structure <FORM:0789033/IV (b)/4> (O = (R) being an aldehyde group with the same number of carbon atoms as R) or by reacting a compound of the general formula <FORM:0789033/IV (b)/5> with a compound of the general formula <FORM:0789033/IV (b)/6> with, in each case, subsequent reduction of the Schiff's base so formed. In examples: (1) 2-(p-methoxyphenyl) - ethylamine with formalin and sodium cyanide in presence of aqueous sodium bisulphite at 60 DEG C. gives, after addition of HCl, 2 - [21 - (p - methoxyphenyl)ethylamino]-acetonitrile hydrochloride, this is reacted with veratrole in presence of HCl gas and AlCl3 in nitrobenzene to give 1-(31:41-dimethoxyphenyl)-2 - [21 - (p - methoxyphenyl) ethylamino] - ethan - 1-one hydrochloride, this is boiled with HBr to give, on addition of HCl, 1-(31:41-dihydroxyphenyl) - 2 - [21 - (p - hydroxyphenyl) ethylamino]-ethan-1-one and this is catalytically reduced to the corresponding secondary alcohol; (2) the processes are as in (1), the intermediates being 2 - [11 - methyl - 21 - (p - methoxyphenyl) ethylamino]-acetonitrile hydrochloride, 1-(31:41-dimethoxyphenyl) - 2 - [11 - methyl - 21 - (p - methoxyphenyl) - ethylamino] - ethan - 1 - one hydrochloride and 1 - (31:41 - dihydroxyphenyl) - 2 - [11 - methyl - 21 - (p - hydroxyphenyl) - ethylamino] - ethan - 1 - one hydrochloride, this last compound then being reduced to the corresponding secondary alcohol; (3) the processes are as in (1), the intermediates being 2-[11-methyl - 31 - (p - methoxyphenyl) propylamino]-acetonitrile hydrochloride, 1 - (31:41 - dimethoxyphenyl) - 2 - [11 - methyl - 31 - (p - methoxyphenyl) - propylamino] - ethan - 1 - one and 1 (31:41 - dihydroxyphenyl) - 2 - [11 - methyl - 31 - (p - hydroxyphenyl) - propylamino] - ethan - 1 - one hydrochloride, this last compound then being reduced to the corresponding secondary alcohol; (4) the processes are as in (1), the intermediates being 2 - [11:11 - dimethyl - 21 - (p - methoxyphenyl) - ethylamino] - acetonitrile hydrochloride, 1 - (31:41 - dimethoxyphenyl) - 2 - [11:11 - dimethyl - 21 - (p - methoxyphenyl) - ethylamino] - ethan - 1 - one hydrochloride and 1 - (31:41 - dihydroxyphenyl) - 2 - [11:11 - dimethyl-21 - (p - hydroxyphenyl) - ethylamino] - ethan - 1 - one hydrochloride, this last compound then being reduced to the corresponding secondary alcohol; (5) 1 - methyl - 2 - (31:41 - dimethoxyphenyl) - ethylamine and 1-(31:41-dibenzyloxyphenyl)-2-bromo-ethan-1-one are condensed in presence of HCl to yield 1-(31:41-dibenzyloxyphenyl)-2-[11-methyl - 21 - (311:411 - dimethoxyphenyl) ethylamino] - ethan - 1 - one hydrochloride, this is catalytically hydrogenated to give 1-(31:41-dihydroxyphenyl) - 2 - [11 - methyl - 21 - (311:411-dimethoxyphenyl) - ethylamino] - ethan - 1 - one hydrochloride, this is boiled with HBr to yield 1 - (31:41 - dihydroxyphenyl) - 2 - [11 - methyl 21 - (311:411 - dihydroxyphenyl) - ethylamino] - ethan-1-one, this is converted to the hydrochloride and this is catalytically hydrogenated to the corresponding secondary alcohol; (6) by similar processes to (5) the following intermediates are prepared:-1-(31:41-dibenzyloxyphenyl) - 2 - [21 - (311 - methoxyphenyl) - - 11 - methyl - ethylamino]-, 1 - (31:41 - dihydroxyphenyl) - 2 - [21 - (311 - methoxyphenyl) - 11 - methyl - ethylamino] - and 1 - (31:41 - dihydroxyphenyl) - 2 - [21 - (311 - hydroxyphenyl) - 11 - methyl - ethylamino] - ethan - 1 - one hydrochlorides, this last compound then being reduced to the corresponding secondary alcohol; (7) similarly 1 - (31:41 - dibenzyloxyphenyl) - 2 - [21 - (211 - methoxyphenyl) - 11 - methyl - ethyl amino]-, 1 - (31:41 - dihydroxyphenyl) - 2 - [21 - (211 - methoxyphenyl) - 11 - methyl - ethylamino] - and 1 - (31:41 - dihydroxyphenyl) - 2 - [21 - (211-hydroxyphenyl) - 11 - methyl - ethylamino] - ethan-1-one hydrochlorides are prepared, the last compound then being reduced to the corresponding secondary alcohol; and (8) 1-methyl-2-(41-benzyloxyphenyl) - ethylamine and 1 - (31:41-dibenzyloxyphenyl) - 2 - bromo - ethan - 1 - one are condensed to yield 1-(31:41-dibenzyloxyphenyl) - 2 - [11 - methyl - 21 - (411 - benzyloxyphenyl) - ethylamino] - ethan - 1 - one hydrochloride and this is catalytically hydrogenated to yield 1-(31:41-dihydroxyphenyl)-2-[11-methyl-21 - (411 - hydroxyphenyl) - ethylamino] - ethanol. Specifications 640,492 and 684,781 are referred to.
GB30015/55A 1954-10-23 1955-10-20 Improvements in or relating to substituted aralkyl-phenyl-alkylamines Expired GB789033A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL789033X 1954-10-23

Publications (1)

Publication Number Publication Date
GB789033A true GB789033A (en) 1958-01-15

Family

ID=19832360

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30015/55A Expired GB789033A (en) 1954-10-23 1955-10-20 Improvements in or relating to substituted aralkyl-phenyl-alkylamines

Country Status (1)

Country Link
GB (1) GB789033A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3164629A (en) * 1961-06-21 1965-01-05 Osterreichische Stickstaffwerk 3', 5'-dialkanoyloxyphenyl-2 aminoethanol-(1) salts
US3180887A (en) * 1961-09-14 1965-04-27 Chemie Linz Ag N-sec lower alkyl 2-(3, 5-diacetoxyphenyl) ethanolamine
US3211792A (en) * 1963-01-24 1965-10-12 Hoffmann La Roche 1-(phenyl)-or 1-(alkyl-substitutedphenyl)-5-(substituted-phenyl)-3-aza penta-(1)-ols and salts thereof
US3250803A (en) * 1961-07-06 1966-05-10 Philips Corp Method of manufacturing the individual racemates of n-(p-hydroxyphenylisopropyl) arterenol and products
US3341593A (en) * 1962-11-30 1967-09-12 Boehringer Sohn Ingelheim 1-p-hydroxyphenyl-2-(beta-3', 5'-dihydroxyphenyl-beta-hydroxy)-ethylamino-propanes
US3406237A (en) * 1962-11-30 1968-10-15 Boehringer Sohn Ingelheim Composition and a method for relieving broncho-spasms which use 1-p-hydroxyphenyl - 2 - (beta - 3',5' - dihydroxyphenyl - beta-hydroxy)-ethylaminopropane
US3542870A (en) * 1967-01-10 1970-11-24 Houde Lab 1 - (3,5 - dihalo - 4 - hydroxy - phenyl) - 2 - (2-aryloxy or 2 - arylalkyl - isopropylamino)-propanols
US4490392A (en) * 1977-08-11 1984-12-25 Tanabe Seiyaku Co., Ltd. Benzylalcohol derivative and process for preparing
US4853381A (en) * 1984-04-17 1989-08-01 Glaxo Group Limited Ethanolamine compounds

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3164629A (en) * 1961-06-21 1965-01-05 Osterreichische Stickstaffwerk 3', 5'-dialkanoyloxyphenyl-2 aminoethanol-(1) salts
US3250803A (en) * 1961-07-06 1966-05-10 Philips Corp Method of manufacturing the individual racemates of n-(p-hydroxyphenylisopropyl) arterenol and products
US3180887A (en) * 1961-09-14 1965-04-27 Chemie Linz Ag N-sec lower alkyl 2-(3, 5-diacetoxyphenyl) ethanolamine
US3341593A (en) * 1962-11-30 1967-09-12 Boehringer Sohn Ingelheim 1-p-hydroxyphenyl-2-(beta-3', 5'-dihydroxyphenyl-beta-hydroxy)-ethylamino-propanes
US3406237A (en) * 1962-11-30 1968-10-15 Boehringer Sohn Ingelheim Composition and a method for relieving broncho-spasms which use 1-p-hydroxyphenyl - 2 - (beta - 3',5' - dihydroxyphenyl - beta-hydroxy)-ethylaminopropane
US3211792A (en) * 1963-01-24 1965-10-12 Hoffmann La Roche 1-(phenyl)-or 1-(alkyl-substitutedphenyl)-5-(substituted-phenyl)-3-aza penta-(1)-ols and salts thereof
US3542870A (en) * 1967-01-10 1970-11-24 Houde Lab 1 - (3,5 - dihalo - 4 - hydroxy - phenyl) - 2 - (2-aryloxy or 2 - arylalkyl - isopropylamino)-propanols
US4490392A (en) * 1977-08-11 1984-12-25 Tanabe Seiyaku Co., Ltd. Benzylalcohol derivative and process for preparing
US4853381A (en) * 1984-04-17 1989-08-01 Glaxo Group Limited Ethanolamine compounds

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