Acetone → 3-Benzyl-2,2-dimethylimidazolidin-4-one

HRID 1675183Notes

Reaction equation

HRID 1675183 reaction equation
[CH2:1]([NH:8][C:9](=[O:12])[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14]([CH3:16])=O.C(N(CC)CC)C>CO>[CH2:1]([N:8]1[C:9](=[O:12])[CH2:10][NH:11][C:14]1([CH3:16])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 8471TriethylamineHCID 111266102-amino-N-benzylacetamide

Product 1

HCID 574330893-Benzyl-2,2-dimethylimidazolidin-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N1-benzylglycinamide (3.00 g, 14.95 mmol) in MeOH (25 mL) were added acetone (5.50 mL, 74.75 mmol) and triethylamine (1.67 mL, 11.96 mmol). The solution was stirred and heated to reflux overnight under an atmosphere of nitrogen. The solvent was removed in vacuo, and the resulting orange oil was purified by flash column chromatography on silica gel using a gradient elution of 0-7% (MeOH/NH3)/CH2Cl2. Collection and concentration of the appropriate fractions afforded the product as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.31-7.27 (m, 5H), 4.44 (s, 2H), 3.55 (s, 2H), 1.26 (s, 6H); ES MS (M+1)=205.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight under an atmosphere of nitrogen
  3. customThe solvent was removed in vacuo
  4. customthe resulting orange oil was purified by flash column chromatography on silica gel using
  5. washa gradient elution of 0-7% (MeOH/NH3)/CH2Cl2
  6. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-e484d7d6f494408c9a853a58e8b6a794
Source dataset
uspto-grants-2011_08
Patent number
US08003653B2

Reaction notes

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