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

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Reaction Steps

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (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 the title compound as a foam (60 mg, 69%) 1H NMR (CDCl3) 7.35-7.22 (m, 5H), 6.78 (d, J=8.8, 1H), 6.49 (br s, 1H), 6.40 (br d, J=7.5, 1H), 4.73-4.70 (m, 1H), 4.27-4.13 (m, 2H), 3.93 (br d, J=12.5, 1H), 3.79 (s, 3H), 3.43-3.00 (m, 7H), 2.75-2.67 (m, 2H), 1.96-1.91 (m, 2H), 1.90-1.79 (m, 3H), 1.64-1.59 (m, 2H), 1.04 (t, J=7.2, 3H). LC/MS (Method A) 6.86 min, [M+1]+ 438.

Provenance & Evidence