Formamide → HCID 15544537, compound

Participants

Reaction Steps

500 mg of 5-(4-benzylpiperazin-1-yl)-2-hydroxybenzaldehyde are added at 20° under nitrogen with stirring to 5 ml of NMP, and 0.25 g of potassium carbonate and 0.2 ml of ethyl bromoacetate are added to the solution. The mixture is stirred at 105° for 15 hours and cooled to 25°. 0.2 ml of formamide is then added to the mixture, and stirring is continued for 30 minutes. 1 ml of sodium methoxide (30% solution in methanol) is then added at 25° over the course of 15 minutes, and the mixture is stirred at 25-30° for a further 3 hours. The reaction mixture is poured into 30 ml of water (10°), the aqueous phase is extracted at 10° with 3×50 ml of ethyl acetate, the combined organic phases are washed with 50 ml of water, and the solvent is removed under reduced pressure (0.7 g of orange oil). The oil is recrystallized from 10 ml of toluene (375 mg of pale-yellow crystals; 66%), m.p. 206-208°; MS 335 (M+), 244, 189, 146, 91 (100%).

Provenance & Evidence