GB787384A - Manufacture of basic compounds - Google Patents

Manufacture of basic compounds

Info

Publication number
GB787384A
GB787384A GB8183/54A GB818354A GB787384A GB 787384 A GB787384 A GB 787384A GB 8183/54 A GB8183/54 A GB 8183/54A GB 818354 A GB818354 A GB 818354A GB 787384 A GB787384 A GB 787384A
Authority
GB
United Kingdom
Prior art keywords
pyridyl
phenyl
propanol
sulphuric acid
heating
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
GB8183/54A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB787384A publication Critical patent/GB787384A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • 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
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • 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
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compounds of the general formula <FORM:0787384/IV (b)/1> (wherein R1 is a heterocyclic radical, R2 an aromatic radical and R3 and R4 are hydrogen or alkyl radicals of at most 4 carbon atoms, and N < represents a primary, secondary or tertiary nitrogen atom which, in the last case, can be a member of a saturated heterocyclic ring system) are prepared by reacting an alkylene oxide of the formula <FORM:0787384/IV (b)/2> with a compound R1-CH2-R2 in the presenc of a strongly basic condensing agent, converting the propanol of the general formula <FORM:0787384/IV (b)/3> so formed, if desired without isolation, into its sulphuric acid ester by addition of the equivalent quantity of sulphuric acid and subsequent heating of the sulphate to 120 DEG C. under reduced pressure or, instead of the heating, removal of the water formed during the esterification by azeotropic distillation with an organic solvent such as toluene, xylene or ortho-dichlorobenzene, and heating the ester at a temperature of at most 200 DEG C. with ammonia or a primary or secondary amine. The condensing agent for the first stage may be an alkali metal, or its amide, hydride, hydroxide or alcoholate, or a hydrocarbon compound of the metal, the reaction preferably being carried out in a benzene hydrocarbon, ether or alkanol as solvent. Reference is made to the use of chlorosulphonic acid instead of sulphuric acid in the esterification stage. The amination is advantageously conducted in aqueous medium at 150 DEG to 180 DEG C. In the examples, 2-benzylpyridine and ethylene oxide give 1-phenyl-1-pyridyl-(21)-propanol-3 and this is converted, with or without isolation, into its sulphuric acid ester, which on heating with, respectively, dimethylamine and morpholine yields 1-phenyl-1 - pyridyl - (21) - 3 - dimethylaminopropane and 1 - phenyl - 1 - pyridyl - (21) - 3 - N - morpholinopropane, the maleates of which are described; 1-(p-chlorophenyl)-1-pyridyl-(21)-propanol - (3) and 1 - phenyl - 1 - quinolyl - (21)-propanol-(3) are prepared similarly and are converted, by similar methods into 1-(p-chlorophenyl) - 1 - pyridyl - (21) - 3 - dimethylaminopropane (and its maleate) and 1-phenyl-1-quinolyl - (21) - 3 - N - morpholinopropane respectively. Reference is also made to the use of 4-benzylpyridine, 2-benzylthiazole, 2-benzylthiophene, 2 - (p - methoxybenzyl)-pyridine and 2 - (o - bromobenzyl) - pyridine as starting materials R1-CH2-R2, to propylene oxide as an a ,b -alkylene oxide starting material and to ammonia, methylamine, ethylamine, diethylamine, butylamine, diethanolamine, pyrrolidine and piperidine as further amines which may be used.
GB8183/54A 1953-03-19 1954-03-19 Manufacture of basic compounds Expired GB787384A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEF11409A DE1110643B (en) 1953-03-19 1953-03-19 Process for the preparation of aminopropane derivatives containing at least one N-heterocyclic radical
DE331691X 1953-03-19

Publications (1)

Publication Number Publication Date
GB787384A true GB787384A (en) 1957-12-04

Family

ID=25810651

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8183/54A Expired GB787384A (en) 1953-03-19 1954-03-19 Manufacture of basic compounds

Country Status (5)

Country Link
CH (1) CH331691A (en)
DE (1) DE1110643B (en)
FR (1) FR1160995A (en)
GB (1) GB787384A (en)
NL (1) NL90373C (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0000322B1 (en) * 1977-07-04 1982-05-05 Astra Läkemedel Aktiebolag Compounds having an anti-depressive or tranquilizing activity, pharmaceutical compositions containing them, and processes and intermediates for their preparation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE563398C (en) * 1930-07-22 1932-11-09 I G Farbenindustrie Akt Ges Process for the preparation of organic nitrogenous compounds
DE744996C (en) * 1940-05-18 1944-02-22 Ig Farbenindustrie Ag Process for the production of diamines
NL73568C (en) * 1947-10-28
DE830193C (en) * 1948-11-09 1952-02-04 Farbwerke Hoechst Vormals Meis Process for the preparation of basic compounds
DE832153C (en) * 1948-11-09 1952-02-21 Farbwerke Hoechst Vormals Meis Process for the preparation of basic compounds

Also Published As

Publication number Publication date
DE1110643B (en) 1961-07-13
FR1160995A (en) 1958-08-18
CH331691A (en) 1958-07-31
NL90373C (en)

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