Hydrochloric Acid → HCID 59856530, compound

Participants

Reaction Conditions

Reaction Steps

N-(1-Benzylpiperidin-4-yl)-2-(3-fluoro-2-nitrophenyl)acetamide (2.19 g, 5.90 mmol) was dissolved in tetrahydrofuran (40 ml). Mixture was warmed to 60° C. Chlorotrimethylsilane (2.7 ml, 21.27 mmol) was added to the mixture followed by lithium borohydride (7.2 ml, 14.40 mmol). Mixture was held at 60° C. for 2 hours with stirring. Reaction was quenched with 2 mL methanol. Water (4.0 ml, 222 mmol) was added to the mixture followed by concentrated hydrochloric acid (4.0 ml, 47.4 mmol). Mixture was warmed to reflux and held with stirring for 3 hours. Mixture was cooled to room temperature. Reaction was made basic with 5 mL 10N sodium hydroxide. Mixture stirred at room temperature for 15 minutes. Reaction layers were partitioned and the aqueous phase was discarded. Organic phase was concentrated by roto-vap. Silica gel chromatography eluting 2M ammonia in methanol-dichloromethane afforded the title compound as grey oil in 38% yield. MS (M+H)+=358.4.

Provenance & Evidence