Water → HCID 11952785, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(2,3-dichlorophenyl)piperazine, hydrochloride (8.0 g) and diisopropylethylamine (10 mL) in dimethyl formamide (50 mL) was heated to 45° C. followed by the addition of 4-chloro-1-(2,3-dihydro-1H-indol-1-yl)butan-1-one (6.7 g). The resulting mixture was heated at 100° C. for 6 h, cooled to room temperature and poured into water. The aqueous phase was extracted with diethyl ether, and the combined organic phases were dried (MgSO4), filtered and evaporated in vacuo to give a black oil (14.2 g). The oil was crystallised from acetone, and the formed crystals were recrystallised from ethanol to give a white crystalline material (3.8 g). Mp 134–136° C. 1H NMR (CDCl3): 1.90–2.05 (m, 2H); 2.45–2.60 (m, 4H); 2.65 (s, 4H); 3.00 (s, 4H); 3.20 (t, 2H); 4.10 (t, 2H); 6.90 (d, 1H); 7.00 (t, 1H); 7.05–7–25 (m, 4H); 8.25 (d, 1H). MS m/z: 418 (MH+), 299, 228, 188.

Provenance & Evidence