4-chloro-N-methylpiperidine → 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-methylpiperidine

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Reaction Steps

A Grignard solution prepared from 13.4 grams (0.1 mole) of 1-methyl-4-chloropiperidine, 2.43 grams (0.1 gram atom) of magnesium and 100 milliliters of tetrahydrofuran is added dropwise with stirring to a cooled solution of 17.0 grams (0.075 mole) of 5-chloro-5H-dibenzo[a,d]cycloheptene in 100 milliliters of tetrahydrofuran. After completion of the addition, stirring is continued for several hours at ambient temperature. The solvent is then vaporized under reduced pressure to obtain a residue which is dissolved in a biphasic mixture of benzene and water. The benzene solution is washed, dried filtered and the solvent vaporized as previously described to obtain the desired 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-methylpiperidine, equational isomer as residue.

Provenance & Evidence