Bibliografische Daten

Dokument GB000000807835A (Seiten: 7)

Bibliografische Daten Dokument GB000000807835A (Seiten: 7)
INID Kriterium Feld Inhalt
54 Titel TI [EN] New tertiary amines and their salts and process for their preparation
71/73 Anmelder/Inhaber PA THOMAE GMBH DR K
72 Erfinder IN
22/96 Anmeldedatum AD 23.09.1955
21 Anmeldenummer AN 746758
Anmeldeland AC GB
Veröffentlichungsdatum PUB 21.01.1959
33
31
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Priorität PRC
PRN
PRD
DE
null
19550701
51 IPC-Hauptklasse ICM
51 IPC-Nebenklasse ICS
IPC-Zusatzklasse ICA
IPC-Indexklasse ICI
Gemeinsame Patentklassifikation CPC C07D 295/03
MCD-Hauptklasse MCM
MCD-Nebenklasse MCS C07D 295/03 (2006.01)
MCD-Zusatzklasse MCA C07D 295/02 (2006.01)
57 Zusammenfassung AB [EN] The invention comprises amines of the general formula <FORM:0807835/IV (b)/1> and acid addition and quaternary salts thereof, wherein R is a hydrogen atom or an alkyl or alkoxy group of 1-6 carbon atoms, R1 and R2 are each an alkyl or hydroxyalkyl group of 1-6 carbon atoms or a cycloalkyl or monocyclic aryl group or an alkyl group of 1-6 carbon atoms bearing a monocyclic aryl substituent or NR1R2 together for a heterocyclic ring which may optionally contain a further hetero-atom and Y is a substituted or unsubstituted aralkyl group or an alkyl group of 3-12 carbon atoms. The amines are prepared by treating an aminopropionitrile of the formula <FORM:0807835/IV (b)/2> with an organomagnesium halide of the formula Hal-Mg-Y, in an inert solvent such as ether, dibutyl ether, dioxan, benzene or benzene/tetrahydrofuran, preferably at the boiling-point of the solvent, and hydrolysing the resulting condensation product to give the amine. The products may be converted into their acid addition salts such as the hydrochloride, hydrobromide, sulphate, phosphate, nitrate, acetate, propionate, butyrate, valerate, oxalate, malonate, succinate, maleate, fumarate, lactate, tartrate, citrate, malate, benzoate, phthalate, cinnamate, salicylate, nicotinate or furan-2-carboxylate or into their quaternary salts with alkyl halides, dimethyl sulphate, diethyl sulphate, alkyl p-toluenesulphonates, cyclohexyl halides or cyclopentyl halides. Preferred products include the o -phenyl derivatives of 4-pyrrolidino-pentane, 4-piperidino-pentane, 5-pyrrolidino-hexane, 3-pyrrolidino-2-methylbutane and 1 - phenyl - 3 - dimethylaminobutane. Specified products prepared in the examples include (a) phenethylamines; a -nonyl - N:N - diethyl -, a - benzyl - N:N - di - n - butyl -, a - phenethyl - N:N - dimethyl -, a - (a - phenylethyl) - N:N - diethyl -, a - phenethyl - N:N - diethyl -, a - phenethyl - N:N - di-n-butyl- and a -p-isopropyl-phenethyl-N:N-diethyl-; (b) morpholines; N-[a -(g -phenylpropyl) - p - methylphenethyl] -, N - [a - (b - p - isopropylphenyl - isopropyl) - phenethyl] - an N - a - isopropyl - phenethyl -; (c) piperidines; N - a - (g - phenylpropyl) - phenethyl - and N - a -propyl-phenethyl-, and (d) pyrrolidines; N-[a - (b - p - isopropylphenyl - isopropyl) - phenethyl] -, N - a - propyl - phenethyl -, N - a - butyl - phenethyl -, N - a - isopropyl - phenethyl -, N - a - (a - phenylethyl) - phenethyl -, N - a - phenethyl - phenethyl -, and N - a - benzyl - phenethyl. a - Tertiary - aminopropionitriles of the formula II used as starting materials, such as 2 - phenyl - 1 - piperidino - propionitrile, 2 - phenyl - 1 - diethylamino - propionitrile and 2 - p - methylphenyl - 1 - morpholino - propionitrile are made by known methods, for example by the reaction of an aldehyde such as a phenyl acetaldehyde with potassium cyanide and an amine of the formula NHR1R2. 3 - (4 - Isopropylphenyl) - 2 - methyl - 1 - pyrrolidino - butyronitrile is made by the action of sodium bisulphite, pyrrolidine and potassium cyanide on cyclamen aldehyde.
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Prüfstoff-IPC ICP C07C 85/22
C07C 85/24
C07D 295/02