C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/292.2, 260/2
C07D 211/58 (2006.01)
Patent
CA 1099719
ABSTRACT Therapeutically useful N-(1-benzylpiperid-4-yl)- benzamides of the formula: Image (wherein X represents a chlorine or bromine atom, R1 represents an alkyl group containing up to 6 carbon atoms, R2 and R3 represent hydrogen atoms or one of those symbols represents a chlorine atom in the 3- or 4-position or a methyl or methoxy group in the 4-position and the other symbol represents a hydrogen atom, or R2 and R3 together represent a methylenedioxy group attached to the 3- and 4-positions) are prepared by a new process which comprises reacting a thiobenzoic acid derivative of the formula: Image V (wherein R4 represents a hydrogen atom, the formyl group, or an alkanoyl radical containing from 2 to 5 carbon atoms optionally carrying one to three halogen atoms as substituents) with an alkyl chlorofonmate containing up to 6 carbon atoms in the alkyl moiety in an organic solvent and in the presence of triethylamine at a temperature between -15°C and 0°C, and reacting the resulting Image VI (wherein R5 represents an alkyl group containing up to 6 carbon atoms) in situ with a 1-benzyl-4-aminopiperidine of the formula: Image IV at a temperature between 0°C and 20°C, and - when R4 in the compound so obtained of the formula: Image VII is the formyl group or an alkanoyl radical as hereinbefore mentioned - subjecting the compound to acid hydrolysis to remove the acyl group and give an N-(1-benzylpiperid-4-yl)-benzamide of general formula I.
317711
Soto Jose Prieto
Spickett Robert G. W.
Anphar S.a.
Fetherstonhaugh & Co.
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