Benzylamine → Hydrochloric Acid

HRID 1438711Notes

Reaction equation

HRID 1438711 reaction equation
[Cl:1]C1CCN(C)C1.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOCC>[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[ClH:1]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 123740953-Chloro-1-methylpyrrolidine

Product 2

HCID 313Hydrochloric AcidHCID 7504Benzylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  1. temperaturegently refluxed at 150° for 8 hr

Sources & evidence

ORD record
ord-5406edb8f5c9421b85dc7e2661b40aa3
Source dataset
uspto-grants-1977_11
Patent number
US04056535

Reaction notes

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