Isopropylamine → HCID 86756661, compound

HRID 1976111Notes

Reaction equation

HRID 1976111 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[CH:5](=O)[CH2:6][CH:7]([CH3:9])[CH3:8].[CH2:11]([N+:18]#[C-:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[O:20]1CCCC1.[C:25]([OH:29])(=O)[CH:26]=[CH2:27]>CO>[CH2:11]([NH:18][C:19]([CH:5]([C:26](=[CH2:27])[C:25]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:29])[CH2:6][CH:7]([CH3:9])[CH3:8])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 6581Acrylic AcidHCID 8028TetrahydrofuranHCID 115523-MethylbutanalHCID 82558Benzyl isocyanide

Product 1

HCID 86756661HCID 86756661, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of isopropylamine (0.43 ml, 5.0 mmol) in methanol (5 ml) was added isovaleraldehyde (0.54 ml, 5.0 mmol). After 15 minutes of stirring a solution of benzylisocyanide in tetrahydrofuran (1N, 5 ml, 5.0 mmol) was added followed by acrylic acid (0.34 ml, 5.0 mmol). The reaction was stirred at room temperature for 72 h, the volatiles were removed in vacuo and the resulting oil dissolved in ethyl acetate (40 ml). The organic mixture was washed with 1N hydrochloric acid (10 ml) and brine (10 ml), dried (Na2SO4) and the solvent evaporated in vacuo. The crude residue was purified by chromatography using a gradient from 30% ethyl acetate/hexane to 50% ethyl acetate/hexane. Pure fraction were collected and the solvent evaporated in vacuo which afforded 1.5 g (100%) of N-(1-benzylcarbamoyl-3-methyl-butyl-N-isopropyl-acrylamide as an oil.

Workup

  1. additionwas added
  2. customthe volatiles were removed in vacuo
  3. dissolutionthe resulting oil dissolved in ethyl acetate (40 ml)
  4. washThe organic mixture was washed with 1N hydrochloric acid (10 ml) and brine (10 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe crude residue was purified by chromatography
  8. customPure fraction were collected
  9. customthe solvent evaporated in vacuo which

Sources & evidence

ORD record
ord-6ae2895166e744b7b741561f6173cc74
Source dataset
uspto-grants-2001_05
Patent number
US06225329B1

Reaction notes

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