Phosgene → HCID 58968698, compound

Participants

Reaction Steps

To a solution of (3,5-bis-trifluoromethyl-benzyl)-[2-(cyclohexyl-methoxy-methyl)-5-trifluoromethyl-benzyl]-amine (Example 41, STEP E, 20 mg, 0.038 mmol) in dichloromethane (1 ml) was added diisopropylethyl amine (6 mg, 0.045 mmol) followed by phosgene (18.8 mg, 0.038 mmol) at room temperature and stirred for 1 hour. Reaction mixture was then treated with concentrated ammonium hydroxide (0.5 ml) and stirred at room temperature for overnight. The reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulphate and concentrated in vacuo. The product was purified on Biotage column (12+S), eluting with 2% ethyl acetate in heptane (1CV), 2-20% (10CV), 20% (2CV) to yield the title compound (7 mg, 30%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.0 (m, 6H) 1.4 (m, 1H) 1.59 (m, 4H) 1.67 (s, 1H) 1.94 (d, J=12.4 Hz, 1H) 3.1 (s, 3H) 3.92 (d, J=7.8 Hz, 1H) 4.6 (m, 4H) 7.36 (s, 1H) 7.45 (d, J=7.9 Hz, 1H) 7.53 (d, J=8.3 Hz, 1H) 7.68 (s, 2H) 7.78 (s, 1H). MS (ES+) Calc: 570.2, Found: 615.6 (M+45).

Provenance & Evidence