Thionyl Chloride → (R)-3-Chloro-1-(4-methoxyphenethyl)-3-methylpiperidine

Participants

Reaction Steps

Thionyl chloride (238 mg) was added slowly to a solution of (S)-2-hydroxymethyl-1-(4-methoxyphenethyl)-2-methylpyrrolidine (see Preparation 10) (349 mg) in dichloromethane (15 ml) and the mixture was heated under reflux for 2 hours. The reaction was cooled, diluted with dichloromethane, washed with 10% aqueous sodium carbonate solution, dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a brown gum, (130 mg), which was characterised by NMR and used directly in Example 4 without further purification.

Provenance & Evidence