D-Tartaric acid → HCID 57889970, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (R)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol, D-(−)-Tartaric Acid (6.2 g, 15.90 mmol) in concentrated hydrochloric acid (150 mL) was refluxed for 27 hours, during which time a clear solution was observed. The solution was cooled to 0° C., which caused a white solid to precipitate, and the pH was adjusted to ˜13 with the slow, careful addition of solid sodium hydroxide. The aqueous was extracted with EtOAc (3×300 mL), the combined organic layers were washed with 1N NaOH (3×100 mL), once with brine (100 mL), then dried over sodium sulfate and concentrated in-vacuo to yield the title compound (3.46 g, 15.60 mmol, 98% yield) as a pale yellow oil. MS (ESI+)=222/224, (M+H)+.

Provenance & Evidence