Sodium Hydroxide → 3-Aminomethyl-1-(p-chlorobenzyl)piperidine

Participants

Reaction Steps

To a solution of 10.52 g of the crude 1-(p-chlorobenzyl)-3-phthalimidomethylpiperidine in ethanol (100 ml) was added hydrazine monohydrate (1.8 ml, 58 mmol) and the mixture was heated under reflux for 2 hours. After cooling, 10% aqueous sodium hydroxide (200 ml) was added to dissolve insolubles and the ethanol was distilled off under reduced pressure. The aqueous layer was extracted with chloroform (150 ml×3) and then the combined organic layer was then extracted with 10% aqueous hydrochloric acid (150 ml×3). The combined aqueous hydrochloric acid layer was washed with chloroform (100 ml), 10% aqueous sodium hydroxide was added until it became strongly basic and then extracted with chloroform (100 ml×3). The combined organic layer was dried over potassium carbonate and the solvent was distilled off under reduced pressure to give crude 3-aminomethyl-1-(p-chlorobenzyl)piperidine (3.93 g). A total yield of two steps=92%. This compound was used for the subsequent reaction without purification.

Provenance & Evidence