Benzyl Bromide → Benzenemethanamine, N-hexyl-

HRID 400203

Reaction equation

HRID 400203 reaction equation
[CH2:1]([NH2:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([NH:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 8102Hexylamine

Product 1

HCID 485395Benzenemethanamine, N-hexyl-Yield 89%

Procedure

A! 200 ml (1.49 moles) of hexylamine cooled to 5° C. were added with benzyl bromide (42.3 ml, 0.35 mole), and the resultant mixture was stirred for 1 hour at room temperature. The hexylamine in excess was then distilled off under vacuum, and the residue dissolved in 300 ml of ethyl ether and washed with 200 ml of 0.5N sodium hydroxide. The ether phase was anhydrified over sodium sulfate and evaporated to dryness thus yielding 75.5 g of a crude which, by distillation under vacuum, gave 59 g (yield: 89%) of N-benzyl-N-hexylamine (b.p.--90°-95° C./0.6 mmHg).

Workup

  1. distillationThe hexylamine in excess was then distilled off under vacuum
  2. dissolutionthe residue dissolved in 300 ml of ethyl ether
  3. washwashed with 200 ml of 0.5N sodium hydroxide
  4. customevaporated to dryness
  5. customthus yielding 75.5 g of a crude which
  6. distillationby distillation under vacuum

Sources & evidence

ORD record
ord-b52e3838c7d1473386d8e76d81f29a25
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Linked notes

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