Morpholine → (2-Amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)-(5-bromothiophen-2-yl)-methanone

Participants

Reaction Steps

The procedure of Example 1 was followed except that 2-acetyl-5-bromothiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(5-bromothiophene-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-bromothiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 72%; IR (KBr) cm−1: 3411, 2923, 1570, 1411, 1314, 978; 1H NMR (CDCl3):δ 2.38 (t, J=5.4 Hz, 2H), 2.59 (t, 2H, J=5.4 Hz), 3.48 (s, 2H), 3.67 (s, 2H), 6.28 (bs, 2H), 7.01 (d, 1H, J=4 Hz), 7.15 (d, 1H, J=4 Hz), 7.32 (m, 5H); brown solid, mp: 87–89° C. (petroleum ether).

Provenance & Evidence