Diisopropylethylamine → 4-[5-(2-Pyridinyl)thien-2-ylcarbonyl]-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

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Reaction Steps

To a cooled solution (0° C.) of 0.23 g of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine, 523 μl of N,N-diisopropylethylamine in 5 ml of dichloromethane is added 0.436 g of 5-(2-pyridinyl)thiophene-2-carbonyl chloride. The mixture is stirred at room temperature for 16 hours under argon and diluted with 40 ml of CH2Cl2 and 20 ml of water. The organic layer is separated and washed with 20 ml each of 1N NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is crystallized from ethyl acetate plus a small amount of hexane to give 0.485 g of tan crystals, m.p. 150°-154° C.

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