Morpholine → HCID 10200324, compound

Participants

Reaction Steps

The procedure of Example 1 was followed except that 2-acetyl-5-chlorothiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(5-chlorothiophene-2-carbonyl)acetonitrile (Steps A and B). 1-Benzyl-4-piperidone (van der Klein et al., (1999) J. Med. Chem. 42: 3629-3635), 2-(5-chlorothiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 63%; IR (KBr) cm−1: 3306, 2956, 2807, 1715, 1574, 1428, 1354, 1122, 1008, 742, 699; 1H NMR (CDCl3):δ2.39 (m, 2H), 2.59 (t, 2H, J=5.2 Hz), 3.45 (s, 2H), 3.67 (s, 2H), 6.26 (bs, 2H), 6.87 (d, 1H, J=3.8 Hz), 7.19 (d, 1H, J=4 Hz), 7.35 (m, 5H); yellow solid, mp: 81-83° C. (petroleum ether).

Provenance & Evidence