Cyclohexanone → (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-thiophen-3-yl-methanone

Participants

Reaction Steps

The procedure of Example 1 was followed except that 3-acetylthiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(thiophene-3-carbonyl)acetonitrile (Steps A and B). Cyclohexanone (Aldrich), 2-(thiophene-3-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 67%; IR (KBr) cm−1: 3323, 3107, 2929, 1576, 1433, 1266, 1151, 1080, 825,726; 1H NMR (CDCl3):δ 1.55 (m, 2H), 1.77 (m, 2H), 2.01 (t, 2H, J=6 Hz), 2.54 (t, 2H, J=6.2 Hz), 6.46 (bs, 2H), 7.28 (m, 2H), 7.58 (t, 1H, J=2.2 Hz); yellow solid, mp: 133–135° C. (petroleum ether).

Provenance & Evidence