GB431786A - Process for the production of diaminoalcohols of the aromatic series - Google Patents

Process for the production of diaminoalcohols of the aromatic series

Info

Publication number
GB431786A
GB431786A GB1171/34A GB117134A GB431786A GB 431786 A GB431786 A GB 431786A GB 1171/34 A GB1171/34 A GB 1171/34A GB 117134 A GB117134 A GB 117134A GB 431786 A GB431786 A GB 431786A
Authority
GB
United Kingdom
Prior art keywords
phenyl
diethylaminoethyl
yield
methyl
hydrogen
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
GB1171/34A
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.)
CHEMISCHE FABRIKEN DR JOACHIM
Original Assignee
CHEMISCHE FABRIKEN DR JOACHIM
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 CHEMISCHE FABRIKEN DR JOACHIM filed Critical CHEMISCHE FABRIKEN DR JOACHIM
Publication of GB431786A publication Critical patent/GB431786A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C215/30Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton

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

Abstract

Diaminoalcohols of the formula RCHOHCH (R<1>)NR<11>R<111>, in which R is an aromatic radicle of the benzene series, R<1> is hydrogen or methyl, R<11> is a dialkylaminoalkyl group, and R<111> is hydrogen or a hydrocarbon radicle, are prepared (1) by treating monoaminoalcohols of the formula RCHOHCH(R<1>)NHR<111> (or their salts) with dialkylaminoalkyl halides or sulphonates (or their salts) in the presence or absence of an acid-binding agent, or (2) by treating halogen ketones of the formula RCOCH(R<1>)X, where X is halogen, with diamines containing a dialkylaminoalkyl group, and subsequently reducing the keto group, or (3) by treating halogenalcohols of the formula RCHOHCH(R<1>)X with diamines containing a dialkylaminoalkyl p group; a modification of method (3) consists in starting from the ethers of the halogenalcohols and subsequently hydrolyzing the ether group. Examples are given in which (1) l - 1 - phenyl - 2 - methylaminopropanol-1 and diethylaminoethyl chloride yield l - 1 - phenyl - 2 - (methyl) (diethylaminoethyl) aminopropanol-1, the dihydroiodide and diprimary phosphate of which are described; (2) 1 - p - methoxyphenyl - 2 - methylaminoethanol-1 and diethylaminoethyl benzenesulphonate yield 1-p-methoxyphenyl-2 (methyl) (diethylaminoethyl)aminoethanol - 1, the dihydrochloride of which is described; (3) racemic 1 - phenyl - 2 - aminopropanol - 1 and diethylaminoethyl p - toluenesulphonate yield racemic 1 - phenyl - 2 - diethylaminoethylaminopropanol - 1, the dihydroiodide of which is described; (4) a -bromopropiophenone and 1 - methylamino - 2 - diethylaminoethane yield 1 - phenyl - 2 - (methyl)(diethylaminoethyl) aminopropanone-1, which is converted into racemic 1 - phenyl - 2 - (methyl) (diethylaminoethyl)aminopropanol-1 (the dihydrochloride of which is described) by reduction with hydrogen at atmospheric temperature and slightly raised pressure in the presence of a palladium and barium sulphate catalyst; (5) 1 - phenyl - 1 - methoxy - 2 - bromopropane and 1 - methylamino - 2 - diethylaminoethane yield the methyl ether of 1 - phenyl - 2 - (methyl)(diethylaminoethyl)aminopropanol-1, which is heated with hydrobromic acid to hydrolyze the ether group; (6) 1 - phenyl - 2 - benzylaminopropanol-1 and diethylaminoethyl chloride yield 1 - phenyl - 2 - (benzyl)(diethylaminoethyl) aminopropanol-1, the dihydrochloride of which is described. The products are of therapeutic value in the treatment of asthma. The Specification as open to inspection under Sect. 91 states that in method (2) above the reaction of the halogenketones with the diamines and the reduction of the keto group may proceed simultaneously. Further, it includes additional examples of the methods described above in which (1) d - 1 - phenyl - 2 - methylaminopropanol - 1 and diethylaminoethyl chloride yield d - 1 - phenyl - 2 - (methyl)(diethylaminoethyl)aminopropanol-1, the dihydroiodide of which is described; (2) l - 1 - phenyl - 2 - methylaminopropanol - 1 and dibutylaminoethyl chloride yield l - 1 - phenyl - 2 - (methyl)(dibutylaminoethyl)aminopropanol - 1, the dihydrochloride of which is described; (3) racemic 1 - phenyl - 2 - methylaminopropanol - 1 and diethylaminoethyl p - toluenesulphonate yield racemic 1 - phenyl - 2 - (methyl)(diethylaminoethyl)aminopropanol - 1; (4) p - methoxy - w - chloroacetophenone and 1 - methylamino - 2 - diethylaminoethane yield p - methoxy - w - (methyl)(diethylaminoethyl)aminoacetophenone, which is converted into 1-p-methoxyphenyl-2-(methyl)(diethylaminoethy)aminoethanol-1 by treatment with hydrogen at a slightly raised pressure in the presence of palladium supported on charcoal. The Specification states also that diaminoalcohols of the formula above (R being defined as an aromatic radicle) are also obtainable (1) by condensing a diketone RCOCOR<1> with a diamine containing a primary and a tertiary amino group (NH2R<11>, where R<11> is a dialkylaminoalkyl group) to yield an azomethine derivative RCOC(R<1>) : NR<11>, which is converted into a diaminoalcohol by simultaneous or subsequent reduction; (2) by condensing a ketoalcohol RCHOHCOR<1> with a diamine NH2R<11> to yield an azomethine derivative RCHOHC(R<1>) : NR<11>, which is similarly converted into a diaminoalcohol by simultaneous or subsequent reduction. In examples of these methods, (1) 1 - phenylpropane - 1 : 2 - dione and 1 - amino - 2 - diethylaminoethane are condensed in the presence of sulphurous acid and zinc dust to yield directly 1-phenyl-2-diethylaminoethylaminopropanol - 1; (2) 1 - phenyl-1-hydroxypropanone-2 and 1-amino-2-diethylaminoethane yield an azomethine derivative which is reduced, without isolation, by treatment with hydrogen in the presence of a palladium catalyst; 1 - phenyl - 2 - diethylaminoethylaminopropanol-1 is again obtained. This subject-matter does not appear in the Specification as accepted.ALSO:Diaminoalcohols of the formula RCHOHCH(R<1>)NR<11>R<111>, in which R is an aromatic radicle of the benzene series, R<1> is hydrogen or methyl, R<11> is a dialkylaminoalkyl group, and R<111> is hydrogen or a hydrocarbon radicle, are prepared by treating halogenketones of the formula RCOCH(R<1>)X, where X is halogen, with diamines containing a dialkylaminoalkyl group, and subsequently reducing the keto group. An example is given in which a -bromopropiophenone and 1-methylamino-2-diethylaminoethane yield 1-phenyl-2-(methyl) (diethylaminoethyl) aminopropanone-1, which is converted into racemic 1-phenyl-2-(methyl) (diethylaminoethyl)-aminopropanol-1 (the dihydrochloride of which is described) by reduction with hydrogen at atmospheric temperature and slightly raised pressure in the presence of a palladium and barium sulphate catalyst. The products are of therapeutic value in the treatment of asthma. The Specification as open to inspection under Sect. 91 states that the reaction of the halogenketones with the diamines and the reduction of the keto group may proceed simultaneously. Further, it includes an additional example in which (1) p-methoxy-o -chloroacetophenone and 1-methylamino-2-diethylaminoethane yield p-methoxy-o -(methyl) (diethylaminoethyl)-aminoacetophenone, which is converted into 1-p-methoxyphenyl-2-(methyl) (diethylaminoethyl)-aminoethanol-1 by treatment with hydrogen at a slightly raised pressure in the presence of palladium supported on charcoal. The Specification states also that diaminoalcohols of the formula above (R being defined as an aromatic radicle) are also obtainable (1) by condensing a diketone RCOCOR<1> with a diamine containing a primary and tertiary amino group (NH2R<11>, where R<11> is a dialkylaminoalkyl group) to yield an azomethine derivative RCOC(R<1>): NR<11>, which is converted into a diaminoalcohol by simultaneous or subsequent reduction; (2) by condensing a ketoalcohol RCHOHCOR<1> with a diamine NH2R<11> to yield an azomethine derivative RCHOHR(R<1>) : NR<11>, which is similarly converted into a diaminoalcohol by simultaneous or subsequent reduction. In an example 1-phenyl-1-hydroxypropanone-2 and 1-amino-2-diethylaminoethane yield an azomethine derivative which is reduced, without isolation, by treatment with hydrogen in the presence of a palladium catalyst; 1-phenyl-2-diethylaminoethylaminopropanol - 1 is obtained. This subject-matter does not appear in the Specification as accepted.
GB1171/34A 1933-01-12 1934-01-12 Process for the production of diaminoalcohols of the aromatic series Expired GB431786A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE431786X 1933-01-12
DEC47477D DE629699C (en) 1933-01-12 1933-02-02 Process for the preparation of benzene series diamino alcohols

Publications (1)

Publication Number Publication Date
GB431786A true GB431786A (en) 1935-07-12

Family

ID=25926314

Family Applications (3)

Application Number Title Priority Date Filing Date
GB1171/34A Expired GB431786A (en) 1933-01-12 1934-01-12 Process for the production of diaminoalcohols of the aromatic series
GB10001/35A Expired GB431848A (en) 1933-01-12 1934-01-12 Process for the production of diaminoalcohols of the aromatic series
GB21574/36A Expired GB461866A (en) 1933-01-12 1936-08-05 Process for the production of diaminoalcohols of the aromatic series

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB10001/35A Expired GB431848A (en) 1933-01-12 1934-01-12 Process for the production of diaminoalcohols of the aromatic series
GB21574/36A Expired GB461866A (en) 1933-01-12 1936-08-05 Process for the production of diaminoalcohols of the aromatic series

Country Status (4)

Country Link
US (1) US2046947A (en)
DE (1) DE629699C (en)
FR (1) FR781017A (en)
GB (3) GB431786A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5250546A (en) * 1984-09-28 1993-10-05 Nippon Chemiphar Co., Ltd. Amino-alcohol derivatives and processes for their preparation

Also Published As

Publication number Publication date
FR781017A (en) 1935-05-08
US2046947A (en) 1936-07-07
GB431848A (en) 1935-07-12
DE629699C (en) 1936-05-09
GB461866A (en) 1937-02-25

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