Hydrochloric Acid → 1-(3-Aminopropyl)-4-diphenylmethylpiperidine

Participants

Reaction Conditions

Reaction Steps

Borane-tetrahydrofuran complex (1.0M in THF, 5.5 ml, 5.5 mmol, 3.5 equiv) was added under argon to neat 3-(4-diphenylmethylpiperidin-1-yl)propionitrile (480 mg, 1.58 mmol, 1.00 equiv). The mixture was stirred at reflux for 5 hours and then cooled to 0° C. Aqueous HCl (6N, 6 mL) was added cautiously, and stirring was continued at room temperature overnight, then at 42° C. for 1.5 hours. The solution was basified to pH 10-11 by addition of 6N aqueous NaOH and extracted with CH2Cl2 (3×50 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, CHCl3 -MeOH-NH3 (2.0M in MeOH) to give 420 mg (86%) of colorless oil, which was characterized spectroscopically.

Provenance & Evidence