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

HRID 2108028Notes

Reaction equation

HRID 2108028 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. (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 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-4abda5f54b054b1d866188a4003616ad
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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