- Prepration of cisapride
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Cisapride, i.e. cis-4-amino-5-chloro-N-[1-[3-(4 fluoro-phenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxy-benzamide, and similar benzamide derivatives, are prepared from novel 1-aryloxyalkyl- or 1-aralkyl-3-arylcarbonyloxy-4-oxo-piperidines, by nuclear substituent re arrangement involving acyl transfer under animal forming conditions, to give the corresponding 1-aryloxyalkyl- or 1-aralkyl-3-hydroxy-4-lower alkoxy-4-arylamido piperidine. This in turn is readily converted to the corresponding 3-oxo-4-arylamido-piperidine by reaction with strong organic acid, which can then be reduced, deprotected and 3-methylated to give the final compound, e.g. cisapride.
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- α-Hydroxydimethylacetal Formation From Aminoketones Using Hypervalent Iodine
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Various β-aminoketones were converted into the α-hydroxydimethylacetal using either o-iodosylbenzoic acid or (diacetoxy) iodobenzene (KOH/CH3OH) without oxidation at 1 deg C, 2 deg C,or 3 deg C, amino groups or at sulfur in the case of a morpholino group.
- Moriarty, Robert M.,Prakash, Om,Karalis, Pauline,Prakash, Indra
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p. 4745 - 4748
(2007/10/02)
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