Ethyl isocyanate → (S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine-1-carboxylic acid ethylamide

Participants

Reaction Steps

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) in CH2Cl2 (0.5 mL) at 0° C. was treated with ethyl isocyanate (19 μL, 0.24 mmol) and stirred for 1 h, then evaporated and the residue purified by silica gel flash chromatography with 50% then 75% EtOAc/hexane as eluant to afford product as a foam (60 mg, 69%) 1H NMR (CDCl3) 1.04 (t, J=7.2, 3H), 1.59-1.64 (m, 2H), 1.79-1.90 (m, 3H), 1.91-1.96 (m, 2H), 2.67-2.75 (m, 2H), 3.00-3.43 (m, 7H), 3.79 (s, 3H), 3.93 (br d, J=12.5, 1H), 4.13-4.27 (m, 2H), 4.70-4.73 (m, 1H), 6.40 (br d, J=7.5, 1H), 6.49 (br s, 1H), 6.78 (d, J=8.8, 1H), 7.22-7.35 (m, 5H). LC/MS 6.86 min, [M+1]+ 438.

Provenance & Evidence