2-Chloro-N,N-dimethylethylamine → HCID 16059350, compound

Participants

Reaction Steps

To a stirred solution of 20 mg (0.043 mmol) of 1-[1-(1-benzyl-2-methyl-1H-indole-3-carbonyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one (the preparation of which is described hereinafter) in DMF (3 ml) at RT, was added 2.0 mg (0.051 mmol) of NaH (60% in oil). The mixture was stirred 20 min. and then 5.6 mg (0.051 mmol) of (2-chloro-ethyl)-dimethyl-amine in 1 ml of DMF was added. The mixture was stirred an additional 5 hours at 50° C. and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (CH2Cl2/MeOH 8/2) afforded 12 mg (50%) of 1-[1-(1-benzyl-2-methyl-1H-indole-3-carbonyl)-piperidin-4-yl]-3-(2-dimethylamino-ethyl)-1,3-dihydro-benzoimidazol-2-one as a viscous oil. ES-MS m/e (%): 536.2 (M+H+).

Provenance & Evidence