Pyridine → (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]methanesulfonamide

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Reaction Steps

Five grams of 3-chloro-2-(2-aminobutyl)thiophene is dissolved in 10 ml of methylene chloride in a 3-neck round bottomed flask blanketed with an inert atmosphere at 0° C. Pyridine (2.2 ml) is added in one portion followed by 2.05 ml of methanesulfonyl chloride. After warming to room temperature, the mixture is stirred for 4 hours before diluting with 100 ml of diethyl ether. The solution is poured into a separatory funnel and washed with water, dilute 2N HCl, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]methanesulfonamide (5.5 g) as an orange oil which solidifies upon standing in a refrigerator overnight. MS: m/z (EI, 70EV) 267 (5%). 1H NMR (200 MHz; CDCl3): δ 1.0 (3H, t, CH3), 1.6 (2H, m, CH2), 2.65 (3H, s, CH3), 3.0 (2H, m, CH2), 3.6 (1H, m, CH), 6.9 (1H, d, CH), 7.2 (1H, d, CH).

Provenance & Evidence