Tetrahydrofuran → 4-[(2,2-Diethoxyethyl)thio]-1-methylpiperidine

Participants

Reaction Conditions

Reaction Steps

Sodium methylate (18.1 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (22 g) in anhydrous tetrahydrofuran (200 ml). After one hour, the diethyl acetal of bromoacetaldehyde (30.3 ml) is added. After 4 hours at room temperature, the solution is heated for 2 hours at 40° C. The insoluble material is filtered off and rinsed with THF. The filtrate is concentrated and then distilled under reduced pressure to give 4-[(2,2-diethoxyethyl)thio]-1-methylpiperidine (36 g; b.p.=104°-108° C. under 0.05 atm) in the form of an oil.

Provenance & Evidence