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

HRID 1088702Notes

Reaction equation

HRID 1088702 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 221617582-[6-[(6-Bromohexyl)oxy]hexyl]pyridine

Product 1

HCID 22161746N-[6-[[6-(2-Pyridinyl)hexyl]oxy]hexyl]benzenemethanamine

Procedure

2-[6-[(6-Bromohexyl)oxy]hexyl]pyridine (4.99 g) was added dropwise to benzylamine (22 ml) at 140° C. under nitrogen. The solution was stirred at 140° for 1 h and distilled under vacuum to remove benzylamine. The residue was partitioned between ethyl acetate (300 ml) and 8% aqueous sodium bicarbonate (200 ml). The dried organic layer was concentrated and the residual oil was purified by FCC eluting with ethyl acetate-triethylamine (100:1) to give the title compound as a pale yellow oil (4.65 g), t.l.c. (ethyl acetate+few drops triethylamine) Rf 0.23.

Workup

  1. distillationdistilled under vacuum
  2. customto remove benzylamine
  3. customThe residue was partitioned between ethyl acetate (300 ml) and 8% aqueous sodium bicarbonate (200 ml)
  4. concentrationThe dried organic layer was concentrated
  5. customthe residual oil was purified by FCC
  6. washeluting with ethyl acetate-triethylamine (100:1)

Sources & evidence

ORD record
ord-7943357c189e47a2a938a150b7705919
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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