Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-08-21
1998-07-21
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D21174
Patent
active
057837023
ABSTRACT:
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.
REFERENCES:
patent: 3647805 (1972-03-01), Ikikura et al.
patent: 4046767 (1977-09-01), Cavella et al.
patent: 4069331 (1978-01-01), Langbein et al.
patent: 4138492 (1979-02-01), Noverola et al.
patent: 4745192 (1988-05-01), Ertl
patent: 4962115 (1990-10-01), Van Daele
Czarkie et al. "Tetrahedron", 1985 41(6) pp. 1049-1056.
G. Hofle, W. Steglich & H. Vorbruggen Angew, Chem. Int. Ed. Engl. 569-583 (1978) "4-Dialkylaminopyridines as Highly Active Acylation Catalysts".
H. Hiemstra & W. Nico Speckamp, Tet. Lett. vol. 24, 1407-1410 (1983) "Completely Regioselective .alpha.-acyliminium Ion Cyclizations with Allyl and Propargyl Silanes".
C.A. Grob & C. Wagner, Hel. Chi. Acta, 1699-1707 (1955) "Die Konkurrierende 1,2-und 1,3-acylwanderung".
G. Fodor & J. Kiss, JACS vol. 72, 3495-3497 (1950) "Acyl Migration O-N in the Diastereomeric 2-aminocyclohexyl Benzoate".
J.H. Dodd et al., Syn. Comm., vol. 23, 1003-1008 (1993) "A Mild, Nonacidic Method for the Conversion of Carboxylic Esters into Oxazolines".
R.O. Hutchins et al., J.O.C., vol. 48, 3 412-3422 (1983) "Stereoselective Reductions of Substituted Cyclohexyl and Cyclopentyl . . . ".
H.C. Brown & S. Krishnmaurthy, Tetrahedron, vol. 35, 567-607 (1979) "Tetrahedron Report Number 64" Forty Years of Hydride Reductions.
G.E. McCasland & Donald A. Smith, "Stereochemistry of Aminocyclonols Synthesis of cis Epimers via Oxazolines The Aminocyclopentanols" J. Am. Chem. Soc. 72, 2190 (1950).
Herbert O. House & Forrest A. Richey, Jr., "Use of Ketoximes Derivatives to Prepare .alpha.-Acetoxyketones", Journal of Organic Chemistry 34, 1430 (1969).
Lu Yee-Fung
Ngooi Teng-Ko
Oudenes Jan
Slemon Clarke
So Raymond
Dahlen Garth M.
Ivy C. Warren
Torcan Chemical Ltd.
LandOfFree
Preparation of cisapride does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Preparation of cisapride, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of cisapride will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1648040