Phenyl isocyanate → HCID 44514436, compound

Participants

Reaction Steps

4-(3-(2-aminoethyl)-1H-indol-2-yl)-1-butyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexylamine (120 mg, 0.255 mmol, mixture of the two possible diastereoisomers in a ratio of approx. 30:70) was mixed in acetonitrile (2.4 ml) with phenyl isocyanate (0.042 ml, 0.386 mmol). After a reaction time of 2 h at 24° C. the reaction mixture was diluted with 1N sodium hydroxide solution (20 ml) and extracted with dichloromethane (4×10 ml). The combined organic phases were dried with Na2SO4 and then filtered. The volatile constituents of the filtrate were completely removed in a vacuum. The residue (yellow solid, 150 mg) was purified by column chromatography [silica gel 60 (25 g); cyclohexane/ethyl acetate 2:1 (300 ml), ethyl acetate/methanol 1:1 (300 ml]. The product was obtained as a white solid with a yield of 115 mg (76%) (melting point 115-120° C., mixture of the two possible diastereoisomers in a ratio of approx. 25:75).

Provenance & Evidence