Dimethylamine → HCID 19921658, compound

Participants

Reaction Steps

To a solution of phenylmethyl (1H-indol-5-yl)carbamate (3.76 g, 14.1 mmol) in ethanol (6 mL) was added dimethylamine (1.75 mL, 40% aq solution) and formaldehyde (1.25 mL, 40% aq solution). The reaction was heated at reflux for 16 h. The solvent was removed in vacuo and the residue treated with 10% Na2CO3 solution and extracted with four portions of ethyl acetate. The combined organic extracts were washed with saturated NaCl solution, dried with Na2CO3, filtered, and concentrated in vacuo. Silica gel chromatography (93:7:0.7 to 90:10:1 CH2Cl2 :MeOH:NH4OH gradient) of the concentrate afforded phenylmethyl [3-[(dimethylamino)methyl]-1H-indol-5-yl]carbamate (2.30 g, 51%).

Provenance & Evidence