Hydrochloric Acid → 2-(4-(4-Fluorophenyl)thiazol-2-yl)ethanamine

Participants

Reaction Steps

2-(4-(4-fluorophenyl)thiazol-2-yl)acetonitrile (400 mg, 1.83 mmol) was dissolved in tetrahydrofuran (10 mL) at room temperature. Borane tetrahydrofuran complex solution (1M in tetrahydrofuran, 9.16 mL, 9.16 mmol) was added and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was cooled to 0° C. and quenched with methanol (5 eq., 0.4 mL). The reaction was allowed to warm to room temperature and 2N HCl was added until the reaction mixture was confirmed acidic by a pH paper. The reaction mixture was then refluxed at 65° C. for 30 min. The reaction mixture was then allowed to cool to room temperature and was concentrated under reduced pressure. The solid obtained was triturated with ether (2×20 mL) and dichloromethane (2×20 mL). 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 (2×100 mL). The organic layer was dried over anhdrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was used directly without any purification in the next step (100 mg, 25% yield). MS (ESI) m/z: Calculated for C11H11FN2S: 222.06. found: 223.1 (M+H)+.

Provenance & Evidence