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

HRID 1032707Notes

Reaction equation

HRID 1032707 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 hydroxide (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. (toluene-ethanol-0.88 ammonia 80:20:2) Rf 0.44.

Workup

  1. temperatureAfter 1 h at 140° the reaction mixture was cooled
  2. custompartitioned between 2M sodium hydroxide (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-2a4e121f12714c638a86e7a3a185c7ff
Source dataset
uspto-grants-1990_09
Patent number
US04959381

Reaction notes

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