Benzylamine → N-[6-[2-(2-Pyridinyl)ethoxy]hexyl]benzenemethanamine

HRID 1886024Notes

Reaction equation

HRID 1886024 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 151669352-(2-((6-Bromohexyl)oxy)ethyl)pyridine

Product 1

HCID 19876743N-[6-[2-(2-Pyridinyl)ethoxy]hexyl]benzenemethanamine

Procedure

2-[2-[(6-Bromohexyl)oxy]ethyl]pyridine (6.3 g) was added to benzylamine (20 ml) at 140° under nitrogen. After 1 h at 140° the reaction mixture was cooled and partitioned between 2M sodium hydroxyde (100 ml) and ether (100 ml). The organic layer was washed with water and brine, dried and concentrated to a yellow oil. The excess benzylamine was removed by distillation under reduced pressure to leave the title compound as a yellow oil (6.8 g), t.l.c. (System A 80:20:2) Rf 0.44.

Workup

  1. temperatureAfter 1 h at 140° the reaction mixture was cooled
  2. custompartitioned between 2M sodium hydroxyde (100 ml) and ether (100 ml)
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated to a yellow oil
  6. customThe excess benzylamine was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3f52ae01a6fc48a1ae51cd00e2490527
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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