Benzylamine → 262856-94-0

HRID 1936211Notes

Reaction equation

HRID 1936211 reaction equation
[Br:1][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:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[BrH:1].[CH2:19]([NH:26][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:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 110124391-[4-[(6-Bromohexyl)oxy]butyl]benzene

Product 1

HCID 22465724262856-94-0Yield 59.8%

Conditions

Temperature
50 °C

Procedure

A mixture comprising 7.34 g (25.53 mmol) 4-(6-bromohexyloxy)butylbenzene and 10.3 ml (94.30 mmol) benzylamine is heated at 125° C. for 8 hr. The benzylamine in excess is distilled off and the residue dissolved in 30 ml methyl ethyl ketone. To the resulting solution, heated to 50° C., is added a solution of 7.43 ml 47% HBr in 50 ml H2O, then it is allowed to stir for 15 min and decanted. The organic phase is evaporated to dryness an the thus obtained residue triturated with Et2O and filtered to yield 5.9 g (59.8%) N-benzyl-6-(4-phenylbutoxy)hexylamine hydrobromide.

Workup

  1. distillationThe benzylamine in excess is distilled off
  2. dissolutionthe residue dissolved in 30 ml methyl ethyl ketone
  3. additionis added a solution of 7.43 ml 47% HBr in 50 ml H2O
  4. customdecanted
  5. customThe organic phase is evaporated to dryness an the thus obtained residue
  6. customtriturated with Et2O
  7. filtrationfiltered

Sources & evidence

ORD record
ord-2a6e037b05da470eb6ba95b1c95f1b03
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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