1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine

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Reaction Steps

1-(3-Chloropropyl)-4-phenyl-1,2,4,6-tetrahydropyridine can be prepared as follows: a solution of 1-bromo-3-chloropropane (6 cc) and 4-phenyl-1,2,3,6-tetrahydropyridine (5.1 g) in acetonitrile (60 cc) is stirred at 25° C. for 20 hours with potassium carbonate (97 g). The mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height) and eluted with a mixture of cyclohexane and ethyl acetate (50--50 by volume), 250-cc fractions being collected. Fractions 7 to 13 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (5 g) in the form of a yellow oil.

Provenance & Evidence