Uses
1-Methyl-4-(3-chloropropyl)piperazine can be used in the preparation of many pharmaceutically active compounds such as antiulcer agents, antitumor agents, antibiotics and anxiolytics.
Synthesis
General procedure: 1-bromo-3-chloropropane (0.25 mL) was slowly added dropwise to a solution of N-methylpiperazine (0.55 mL) in toluene (2.5 mL) and the reaction was stirred at 80°C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and acidified by slowly adding 2 mol/L hydrochloric acid solution. The aqueous phase was separated and the pH was adjusted to 12 with 2 mol/L aqueous sodium hydroxide solution, followed by the addition of ethyl acetate for extraction. The organic phase was collected, washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give 1-(3-chloropropyl)-4-methylpiperazine (187 mg) as a white solid.1H-NMR (CDCl3) δ: 3.59 (2H, t, J = 6.6 Hz), 2.49 (8H, t, J = 7.3 Hz), 2.29 (3H, s), 1.95 (2H, t, J = 6.9 Hz).
References
[1] Pharmazie, 2005, vol. 60, # 6, p. 411 - 414
[2] Synthetic Communications, 2003, vol. 33, # 14, p. 2483 - 2486
[3] Pharmazie, 1980, vol. 35, # 2, p. 69 - 72
[4] Pharmaceutical Chemistry Journal, 1998, vol. 32, # 7, p. 362 - 369
[5] Farmaco, 1993, vol. 48, # 12, p. 1641 - 1648
