Method for preparing 4-amino-4-phenylpiperidines

Details Method for preparing 4-amino-4-phenylpiperidines Method for preparing 4-amino-4-phenylpiperidines

2006-05-16

2006-05-16

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S244000, C546S192000

Reexamination Certificate

active

07045630

ABSTRACT:
The invention relates to a process for preparing a 4-amino-4-phenylpiperidine (I):in which R is hydrogen or a (C1–C3)alkyl group, characterized in that a 1-protected 4-piperidone (II):in which Pr′ represents a removable N-protecting group, is treated sequentially first with an alkali metal cyanide and then with an amine ENHPr″ (III) in which E represents a group R′=(C1–C3)alkyl, or an N-protecting group and Pr″ is an N-protecting group, the protecting group(s) being removable under the same conditions as Pr′; then the compound thus obtained (IV) is subjected to a Grignard reaction with a phenylmagnesium halide, the two or three protecting groups are removed from the compound thus obtained (V) and compound (I) is isolated or in the form of the free base, which is converted into one of its salts.

REFERENCES:
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patent: WO 01/07050 (2001-02-01), None
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Bert Hermans, et al., 4-Substituted Piperidines. II. Reaction of 1-Benzyl-4-Cyano-4-t-aminopiperidines with Organometallic Compounds, J. Med. Chem. (1965, pp. 851-855, vol. 8).
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