Hydrochloric Acid → 2-(4-(4-Fluorophenyl)thiazol-2-yl)propan-1-amine

Participants

Reaction Steps

To a stirred solution of 2-(4-(4-fluorophenyl)thiazol-2-yl)propanenitrile (140 mg, 0.6 mmol) in THF (3 mL) at room temperature was added borane (1M in THF; 3.01 mL, 3.01 mmol) and the reaction mixture was stirred at room temperature for 1 h and then heated at 40° C. for 1 h. The reaction mixture was then cooled to 0° C. and quenched with MeOH (˜5 eq, ˜0.2 mL), and allowed to warm to room temperature where 2N HCl solution was added until the pH ˜2. The reaction mixture was refluxed at 65° C. for 15 min and then cooled to room temperature and concentrated under reduced pressure. The solid obtained was triturated with ether twice and dichloromethane another two times. The remaining solid was dissolved in water (˜50 mL) and basified to pH ˜11 with NaOH pellets. The aqueous mixture was then extracted with ether and dried over sodium sulfate and concentrated under reduced pressure to give 2-(4-(4-fluorophenyl)thiazol-2-yl)propan-1-amine (75 mg, yield 52%), which was carried through without further purification; MS (ESI) m/z: Calculated for C12H13FN2S: 236.08. found: 237.1 (M+H)+.

Provenance & Evidence