Acetic Acid → HCID 22603068, compound

Participants

Reaction Steps

A solution of 1-(4-Fluorophenyl)-N-methyl-1H-indole-5-carboxamide (3) (12.3 g) in a mixture of acetic acid (60 mL) and trifluoroacetic acid (15 rnL) was added during 0.5 h to a refluxing solution of 4-piperidon, HCl, H2O (36.6 g) in a mixture of acetic acid (50 mL) and trifluoroacetic acid (100 mL). The reaction mixture was refluxed for 1h, cooled to room temperature and the solvents were removed in vacuo. Water was added and pH was adjusted to 10 by addition of aqueous NaOH. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and brine and dried over MgSO4. Evaporation of the solvents in vacuo afforded the title compound as a foam.Yield 16 g. 1H-NMR (DMSO) 2.48 (s, broad, 2H), 2.80 (d. 3H), 2.98 (t, 2H), 3.50 (d, 2H), 6.40(s, 1H) 7.45 (t, 2H), 7.50 (d, 1H), 7.65 (dd, 2H), 7.70-7.80 (m, 2H), 8.40 (s, 1H), 8.45 (q, broad, 1H)

Provenance & Evidence