Benzylamine → HCID 14549839, compound

HRID 1165280Notes

Reaction equation

HRID 1165280 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:25]=[CH:24][C:16]([C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:20]([N:19]([CH2:22][CH3:23])[C:17](=[O:18])[C:16]1[CH:24]=[CH:25][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:14][CH:15]=1)[CH3:21]

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 200714174-{4-[(6-Bromohexyl)oxy]butyl}-N,N-diethylbenzamide

Product 1

HCID 14549839HCID 14549839, compoundYield 76.5%

Procedure

4-[4-[(6-Bromohexyl)oxy]butyl]-N,N-diethybenzamide (6.0 g) and benzylamine (9.36 g) were stirred under nitrogen at 120° for 30 mins. Excess benzylamine was removed by distillation under reduced pressure. The residual solid was dissolved in ethyl acetate (100 ml) and washed with 8% aqueous sodium bicarbonate (100 ml). The ethyl acetate solution was dried and evaporated to give a yellow oil which was purified by FCC eluting System B (95:5:1) to give the title compound as a yellow oil (4.88 g), t.l.c. (System B 95:5:1) Rf 0.15.

Workup

  1. customExcess benzylamine was removed by distillation under reduced pressure
  2. dissolutionThe residual solid was dissolved in ethyl acetate (100 ml)
  3. washwashed with 8% aqueous sodium bicarbonate (100 ml)
  4. dry with materialThe ethyl acetate solution was dried
  5. customevaporated
  6. customto give a yellow oil which
  7. customwas purified by FCC
  8. washeluting System B (95:5:1)

Sources & evidence

ORD record
ord-4a4146e0d23042d298e7249cac6b6311
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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