Morpholine → (2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(5-bromothio-phen-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). Cyclopentanone (Aldrich), 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: 73%; IR (KBr) cm−1: 3349, 3236, 3130, 1590, 1549, 1431, 1414, 1269, 975; 1H NMR (CDCl3):δ 2.285 (m, 2H), 2.51 (t, 2H, J=7.4 Hz), 2.70 (t, 2H, J=7.4 Hz), 6.64 (bs, 2H), 7.02 (d, 1H, J=4 Hz), 7.13 (d, 1H, J=4 Hz); red solid, mp: 154–156° C. (petroleum ether).

Provenance & Evidence