GB687189A - New ethers and process for the production thereof - Google Patents

New ethers and process for the production thereof

Info

Publication number
GB687189A
GB687189A GB533/51A GB53351A GB687189A GB 687189 A GB687189 A GB 687189A GB 533/51 A GB533/51 A GB 533/51A GB 53351 A GB53351 A GB 53351A GB 687189 A GB687189 A GB 687189A
Authority
GB
United Kingdom
Prior art keywords
isopropylaminopropane
methylaminopropane
alkyl
hydrogen
production
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
GB533/51A
Inventor
Hans Suter
Hans Zutter
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.)
Cilag AG
Original Assignee
Cilag AG
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 Cilag AG filed Critical Cilag AG
Publication of GB687189A publication Critical patent/GB687189A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0687189/IV (b)/1> and their salts; R1 is C1-C3 alkyl, R2 is hydrogen, methyl or ethyl, R3 is C1-C6 alkyl, Z is oxygen or sulphur and R4-R6 are hydrogen, halogen, hydroxy, alkyl or alkoxy (not more than 9 carbon atoms in R4-R6 together). These are made by reacting a ketone <FORM:0687189/IV (b)/2> with R3NH2 (or its formate or N-formyl derivative) in the presence of formic acid or catalytically activated hydrogen, and if necessary hydrolysing off the formyl group. The above ketones are obtained from phenols or thiophenols and a -haloketones. Examples show the production of 1-phenoxy-2-methylaminopropane, 1-phenoxy-2-isopropylaminopropane, 1 - (p - hydroxyphenoxy) - 2 - methylaminopropane, 1 - (o - hydroxyphenoxy) - 2 - isopropylaminopropane, 1 - (o - methoxyphenoxy)-2 - methylaminopropane, 1 - (o - methoxyphenoxy) - 2 - isopropylaminopropane, 1 - mesityloxy - 2 - isopropylaminopropane, 1 - (p - chlorophenoxy) - 2 - isopropylaminopropane, 1 - (o - chlorophenoxy) - 2 - isopropylaminopropane, 1 - phenylthio - 2 - isopropylaminopropane and 1 - [21 : 51 - dimethoxyphenoxy) - 2 - methylaminopropane. Salts described are hydrochloride, picrate and p-aminosalicylate.
GB533/51A 1950-01-17 1951-01-08 New ethers and process for the production thereof Expired GB687189A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH687189X 1950-01-17

Publications (1)

Publication Number Publication Date
GB687189A true GB687189A (en) 1953-02-11

Family

ID=4528955

Family Applications (1)

Application Number Title Priority Date Filing Date
GB533/51A Expired GB687189A (en) 1950-01-17 1951-01-08 New ethers and process for the production thereof

Country Status (2)

Country Link
FR (1) FR1045620A (en)
GB (1) GB687189A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2967201A (en) * 1958-06-02 1961-01-03 Lilly Co Eli Alkylaminoalkyl ethers of phenols
US3235597A (en) * 1963-08-12 1966-02-15 Lilly Co Eli N-aryloxyalkyl and arylthioalkyl derivatives of cyclopropylamine
US3515741A (en) * 1964-04-20 1970-06-02 Boehringer Sohn Ingelheim 1-cyanophenoxy-2-amino-alkanes
US4105796A (en) 1975-06-02 1978-08-08 Boehringer Ingelheim Gmbh Pharmaceutical compositions containing racemic or optically active 1-(2,6-dimethyl-phenoxy)-2-methylamino-propane and method of use

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2967201A (en) * 1958-06-02 1961-01-03 Lilly Co Eli Alkylaminoalkyl ethers of phenols
US3235597A (en) * 1963-08-12 1966-02-15 Lilly Co Eli N-aryloxyalkyl and arylthioalkyl derivatives of cyclopropylamine
US3515741A (en) * 1964-04-20 1970-06-02 Boehringer Sohn Ingelheim 1-cyanophenoxy-2-amino-alkanes
US4105796A (en) 1975-06-02 1978-08-08 Boehringer Ingelheim Gmbh Pharmaceutical compositions containing racemic or optically active 1-(2,6-dimethyl-phenoxy)-2-methylamino-propane and method of use

Also Published As

Publication number Publication date
FR1045620A (en) 1953-11-30

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