Hydrochloric Acid → HCID 9870142, compound

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Reaction Steps

4-(4-But-2-ynyloxy-phenylsulfanyl)-piperidine-4-carboxylic acid hydroxy-amide (prepared by the procedure outlined in example 15) (0.15 g, 0.5 mmol) in methanol (5 mL) and dimethylformamide (2.5 mL) was treated with triethylamine (0.15 mL, 1.1 mmol) followed by 4-bromobenzylbromide (0.13 g, 0.53 mmol). After 6 h the solution was diluted with ethyl acetate, acidified to pH=6 with 1N aqueous hydrochloric acid, washed sequentially with water, aqueous sodium bicarbonate and brine and dried over anhydrous sodium sulfate. Concentration in vacuo gave 1-(4-bromo-benzyl)-4-(4-but-2-ynyloxy-phenylsulfanyl)-piperidine-4-carboxylic acid hydroxyamide. 1HNMR (DMSO-d6): 1.5-1.6 (m, CHH, 2H), 1.8 (s, CH3, 3H), 1.9-2.2 (m, CHH, 4H), 2.5-2.6 (m, CHH, 2H), 3.4 (s, CH2Ar, 2H), 4.75 (s, CH2, 2H), 6.9 (d, ArH, 2H), 7.2 (d, ArH, 2H), 7.3 (d, ArH, 2H), 7.5 (d, ArH, 2H), 8.8 (s, NHOH, 1H), 10.6 (d, NHOH, 1H). Electrospray Mass Spectroscopy: ((M+H)+=489/491).

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