1-Bromo-3-chloropropane → 1-[(4-Chlorophenyl)methyl]-4-(3-chloropropyl)piperazine

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Reaction Steps

A mixture of 1-(4-chlorobenzyl)piperazine (6.32 g; 0.03 mole), 1-bromo-3-chloropropane (4.75 g; 0.03 mole), anhydrous potassium carbonate (6.25 g; 0.045 mole) and butanone (75 ml) was stirred at reflux for 3 hr, cooled and filtered. The filtrate was evaporated in vacuo, and the residue dissolved in ether and washed with water (3x). The solvent solution dried over magnesium sulphate, filtered and evaporated to yield 6.86 g (80%) of the title compound. G.L.C. (5% Dexsil 300, 100°-350° at 15°/min) showed the sample to be 99% pure. A sample was distilled b.p.0.5 150°, and the distillate had the following spectral and analytical characteristics: νmax (film) 2900, 2760, 1480, 1450, 1435 cm-1. δ (CDCl3), 1.95 (2H,m); 2.43 (10H,m); 3.42 (2H,s); 3.56 (2H,t,J 7 Hz); 7.25 (4 H,s) (Found; C, 58.32; H, 7.07; Cl, 24.37; N, 9.79; C14H20Cl2N2 requires; C, 58.34; H, 7.02; Cl, 24.69; N, 9.75%).

Provenance & Evidence