Isobutylamine → HCID 53656947, compound

HRID 1955081Notes

Reaction equation

HRID 1955081 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH2:13]([NH2:17])[CH:14]([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][NH:17][CH2:13][CH:14]([CH3:16])[CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 62576Benzyl bromoacetate

Product 1

HCID 53656947HCID 53656947, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an ice-cooled solution of benzyl bromoacetate (17.1 g, 74.6 mmol) in toluene (200 ml) was added isobutylamine (14.8 ml, 150 mmol) with stirring. The reaction mixture was allowed to warm to room temperature then heated at reflux for 1.5 h before leaving to cool to room temperature overnight. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with brine. The organic phase was dried (anhydrous MgSO4), filtered and evaporated to an oil which was purified further by column chromatography (silica gel, 25% ethyl acetate in hexane) to give the title compound as a yellow oil (8.96 g, 54%). 1H-NMR; δ(CDCl3), 7.35 (5H, m), 5.18 (2H, s), 3.45 (2H, s), 2.41 (2H, d, J=6.8 Hz), 1.74 (2H, m) and 0.92 (6H, d, J=6.8 Hz).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 1.5 h
  3. custombefore leaving
  4. temperatureto cool to room temperature overnight
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with brine
  8. dry with materialThe organic phase was dried (anhydrous MgSO4)
  9. filtrationfiltered
  10. customevaporated to an oil which
  11. customwas purified further by column chromatography (silica gel, 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7654e1d19f0b4c5c9b5e6f8b71fe5d39
Source dataset
uspto-grants-2000_09
Patent number
US06124329

Reaction notes

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