Water → HCID 18672412, compound

Participants

Reaction Steps

1M LAH in ether (0.42 mL, 0.42 mmol) was added to a stirred solution of 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzonitrile (67.8 mg, 0.28 mmol) in ether (5 ml) at 0° C. After 1 h the reaction was treated successively with water (16 μL), 15% NaOH (16 μL), and water (32 μL). After stirring for 15 min the mixture was filtered and the filtrate was evaporated. The residue was partitioned between 1N HCl and ether. The aqueous layer was made neutral with NaHCO3 and was extracted with CH2Cl2. The organic layer was dried with Na2SO4 and evaporated to give 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzylamine (61 mg) as a glass: 1H NMR (CDCl3, 400 MHz) δ 3.56 (t, J=11.9 Hz, 4H), 3.73 (s, 2H), 3.85 (s, 2H), 7.26 (m, 3H).

Provenance & Evidence