Dimethylformamide → HCID 69419456, compound

Participants

Reaction Conditions

Reaction Steps

1.95 g (6.13 mmol) of 4-benzylpiperidinyl indole-5-carboxamide was dissolved in 30 mL dry DMF and was treated with 320 mg (8 mmol, 60% suspension in oil) sodium hydride for 30 minutes. The reaction mixture was cooled to 0° C. and 1.225 g (8 mmol) bromomethylacetate was added and stirring continued for 1 h at 0° C. The ice-bath was removed and stirring continued for another 6 h at room temperature. The reaction was quenched by the addition of sat. ammonium chloride solution, diluted with water and extracted with dichloromethane. The extract was dried, evaporated and the residue purified by column chromatography on silica gel eluting with ethylacetate-hexane (25 -35% ethylacetate) to yield 2.2 g ( 92%) of the desired product. MS: M+, 390; M+-1, 389. 1HNMR (CDCl3): □ 7.7 (s, 1H); 7.35-7.1 (m, 8H); 6.6 (s, 1H); 5.1 (s, 2H); 3.75 (s, 3H); 3.0-2.7 (br, m, 4H); 2.6 ( d, 2H); 1.9-1.2 9m, 5H).

Provenance & Evidence