Triphenylphosphine → 3-(4-Phenylthiazol-2-yl)propan-1-amine

Participants

Reaction Steps

Triphenylphosphine (485 mg, 1.85 mmol) was added to a solution of 2-(3-azidopropyl)-4-phenylthiazole (0.3 g, 1.23 mmol) in THF—H2O (10 mL, 8:2 v/v) at 0° C. The reaction mixture was allowed to warm up to room temperature, stirred for 8 h and then concentrated under reduced pressure. The residue was diluted with 1.5N HCl and the aqueous layer was washed with CH2Cl2. The pH of the aqueous layer was adjusted to ˜8-9 using 10% NaOH solution and the organic product was extracted with CH2Cl2. The combined extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 3-(4-phenylthiazol-2-yl)propan-1-amine (240 mg, yield 89%) as a pale yellow liquid, which was carried through without further purification. MS (ESI) m/z: Calculated for C12H14N2S: 218.09. found: 219.2 (M+H)+.

Provenance & Evidence