Dimethylformamide → 3-[3-(4-Methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

POCl3 (1.8 mL, 18.9 mmol) was added dropwise to N,N-dimethylformamide (DMF, 3.8 mL, 51.6 mmol) at −5° C. The mixture was then allowed to come to room temperature and then stirred for 30 minutes after which it was again cooled to −5° C. A solution of 3-[3-(4-methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole (4.5 g, 17.2 mmol) in DMF (9 mL) was added dropwise. The mixture was again allowed to come to room temperature and then stirred at that temperature overnight. The reaction was then quenched with ice, followed by 10 N NaOH to adjust the pH to 10-11. After stirring at room temperature for 1 hr, the reaction was extracted with ethyl acetate (EtOAc), the organic layer separated, washed with brine, dried and concentrated to give 3.1 g (62%) of 3-[3-(4-methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde.

Provenance & Evidence