Benzylamine → N-[6-[3-(2-Pyridinyl)propoxy]hexyl]benzenemethanamine

HRID 1088709Notes

Reaction equation

HRID 1088709 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 221617422-[3-[(6-Bromohexyl)oxy]propyl]pyridine

Product 1

HCID 22161747N-[6-[3-(2-Pyridinyl)propoxy]hexyl]benzenemethanamine

Procedure

2-[3-[(6-Bromohexyl)oxy]propyl]pyridine (17.0 g) was added to benzylamine (50 ml) at 140° under nitrogen. After 1 h at 140° the reaction mixture was cooled and partitioned between 2N sodium hydroxide (250 ml) and ether (250 ml). The organic layer was washed with water and brine, dried and concentrated to a yellow oil. The excess benzylamine was removed by distillation to give the title compound as a yellow oil (18.5 g), t.l.c. (System A 80:20:2) Rf 0.42.

Workup

  1. temperatureAfter 1 h at 140° the reaction mixture was cooled
  2. custompartitioned between 2N sodium hydroxide (250 ml) and ether (250 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

Sources & evidence

ORD record
ord-8f816e48f65d4adcb039330ec9a6cb50
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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