Benzylamine → Hydrochloric Acid

Participants

Reaction Steps

Compound 3-chloro-1-methyl pyrrolidine, 1.33 g (0.0111 mol), and 6.9 ml (6.3 g, 0.063 mol) benzylamine were combined and gently refluxed at 150° for 8 hr. Et2O was added to the cooled reaction and the white solid that formed (benzylamine.HCl) was filtered. The filtrate was distilled at atmospheric pressure to remove Et2O, then at water aspirator vacuum to remove benzylamine (bp 78°-85°) and then at 0.1 mm Hg to yield 1.24 g (52%) colorless liquid, bp 85°-88°. This was dissolved in 150 ml Et2O, treated with 2.3 ml 6N ethanolic HCl, stirred in ice for 1 hr, and filtered. Trituration in hot abs. EtOH followed by filtration yielded 0.55 g white solid, mp 105°-110°. An additional 0.1 g crystallized from the mother liquor, mp 113°-118°. A white solid weighting 0.5 g, mp 90°- 98°, was precipitated from the mother liquor with Et2O. The HCl.salt, mp 113°-118°, analyzed as an hydrate. Analysis calculated for C12H18N2.2HCl.H2O (percent): C, 51.25; H, 7.89; N, 9.96. Found (percent): C, 51.04; H, 7.61; N, 9.78.

Provenance & Evidence