1-Chloroethyl chloroformate → HCID 69981714, compound

Participants

Reaction Conditions

Reaction Steps

To a magnetically stirred solution of (+/−)-3-(2-dimethylaminomethyl-1-methoxy-cyclohexyl)-benzonitrile (0.10 g, 0.367 mmol) in anhydrous dichloroethane (2 mL) at room temperature under Ar atmosphere was added 1-chloroethyl chloroformate (0.059 mL, 0.825 mmol). After stirring at 100° C. for 2 hours, the reaction was concentrated in vacuo to a crude solid. MeOH (5 mL) was added and the reaction mixture was stirred at 90° C. for 2 hours. The reaction mixture was concentrated in vacuo to a crude oil. The pure amine was obtained by column chromatography over silica gel (0.5:100 TEA/EtOAc as eluent) which gave the free base (0.10 g, 94%). 1H NMR (CDCl3) 1.64-2.09 (m, 11H), 2.17 (s, 3H), 2.33 (m, 1H), 3.16 (s, 3H), 7.47 (d, J=7.6 Hz, 1H), 7.55 (m, 2H), 7.61 (m, 1H). 13C NMR (75 MHz, CDCl3) 21.6, 25.9, 26.6, 32.4, 36.7, 48.3, 50.3, 52.9, 80.7, 112.4, 119.2, 129.1, 130.3, 130.4, 131.1, 145.9.

Provenance & Evidence