Benzylamine → HCID 19876765, compound

HRID 1886022Notes

Reaction equation

HRID 1886022 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOCC>[O:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 19876740HCID 19876740, compound

Product 1

HCID 19876765HCID 19876765, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-[2-[(6-bromohexyl)oxy]ethyl]benzoxazole (1.55 g) in benzylamine (6 ml) was heated at 125° for 2 h under nitrogen, cooled, diluted with ether (100 ml) and the ether suspension washed with 8% sodium bicarbonate solution (25 ml). The organic phase was dried and evaporated in vacuo. Benzylamine was removed by bulb to bulb distillation (b.p. 130°/25 mm) to leave a product which was purified by chromatography over silica (Merck 60) eluting with System B (89:10:1) to afford the title compound as a red oil (250 mg), t.l.c. (System A 39:10:1) Rf 0.55.

Workup

  1. temperaturecooled
  2. washthe ether suspension washed with 8% sodium bicarbonate solution (25 ml)
  3. customThe organic phase was dried
  4. customevaporated in vacuo
  5. customBenzylamine was removed by bulb to bulb distillation (b.p. 130°/25 mm)
  6. customto leave a product which
  7. customwas purified by chromatography over silica (Merck 60)
  8. washeluting with System B (89:10:1)

Sources & evidence

ORD record
ord-071f0dd2ceb342a7a43870665a075f76
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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