Piperidinesynthesis

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Piperidine moiety is very critical part for many CNS agents. It is difficult not touching piperidines as long as your are doing CNS drug study.

1. Personal procedure
2. Nucleophilic addition, elimination and reduction.
3. Coupling, and reduction.
4	J. Med. Chem. 2005, 48, 1781
5	J. Med. Chem. 2005, 48, 1781
6. Alkylation.
7.	Tetrahedron Lett. 2000, 41, 3705-3708

Procedure 1. BnBr (1 equiv.) and 4,4'-bipyridine were dissolved into acetone. The mixture was stirred for 36 hours at room temperature. The precipitate was collected. The precipitate was dissolved into methanol. NaBH4 was added into the methanol solution in portion. The mixture was stirred at 0oC for 1 hour, and another 3 hours at room temperature. Water was added into the mixture to quench the reaction. The product was extracted with ethyl acetate. The organic layer was dried, and concentrated. The resulting residue was purified by silica gel column. The purified product was hydrogenation to piperidine.

Procedure 6. BnCN (1 equiv.) was dissolved into DMF with NaH (6 equiv.). The mixture was heated to 60oC for 1 hour. The alkylation reagent (0.95 equiv.) was added into the mixture slowly. The mixture was refluxed for 6 hours. The reslting mixture was diluted with ethyl acetate and washed with brine. The ethyl acetate solution was dried, and concentrated. The residue was separated by silica gel column. Demethylation with 1-chloroethyl chloroformate to yield piperidine.