Benzylamine → Benzenemethanamine, N-[6-(3-butynyloxy)hexyl]-

HRID 1825306Notes

Reaction equation

HRID 1825306 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Br)[CH2:2][C:3]#[CH:4].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([NH:20][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][C:3]#[CH:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 113792816-Bromohexylbut-3-ynyl ether

Product 1

HCID 22145668Benzenemethanamine, N-[6-(3-butynyloxy)hexyl]-Yield 105.8%

Procedure

A mixture of 6-bromohexyl but-3-ynyl ether (21.5 g) and benzylamine (49.3 g) was heated at 120° for 2 h. The mixture was cooled and partitioned between 2M hydrochloric acid (40 ml) and ethyl acetate (2×200 ml). The combined extracts were washed with an aqueous sodium bicarbonate solution (100 ml), water (200 ml) and dried (Na2SO4). The solvent was removed in vacuo and the residue was purified by chromatography (Merck 9385) eluting with 2% methanol/chloroform. The appropriate fractions were evaporated to give the title compound (25.3 g). LCMS RT=2.2 min.

Workup

  1. temperaturewas heated at 120° for 2 h
  2. temperatureThe mixture was cooled
  3. custompartitioned between 2M hydrochloric acid (40 ml) and ethyl acetate (2×200 ml)
  4. washThe combined extracts were washed with an aqueous sodium bicarbonate solution (100 ml), water (200 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography (Merck 9385)
  8. washeluting with 2% methanol/chloroform
  9. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-cdf7ea4f5f4144249ce7c9a32bff90b4
Source dataset
uspto-grants-2006_05
Patent number
US07045658B2

Reaction notes

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