Benzyl Chloride → 1-Benzylazepan-2-one

HRID 1681997Notes

Reaction equation

HRID 1681997 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C(=O)N(C)C.[H-].[Na+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O>[CH2:19]([N:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]1=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 7768CaprolactamHCID 12437TetramethylureaHCID 24758Sodium hydride

Product 1

HCID 14910681-Benzylazepan-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

33.9 g (0.3 mol) of caprolactam are dissolved in 200 ml of absolute dimethylsulphoxide and 100 ml of absolute tetramethyl urea and 14.4 g (0.33 mol) of 55% sodium hydride/oil dispersion is added in batches. The resulting jelly-like precipitate is stirred for 2 hours at ambient temperature. Then 38 g=34.4 ml (0.3 mol) of benzyl chloride are added dropwize, the mixture is stirred for 2 hours at ambient temperature and then poured onto ice water. The aqueous phase is extracted twice with ethyl acetate. The organic phases are combined, washed four times with water, dried over magnesium sulphate and concentrated by evaporation in vacuo. The residue remaining is distilled in vacuo. Yield: 49.9 g (81.8% of theory), Bp 0.27 mm Hg: 110°-114° C.

Workup

  1. stirringthe mixture is stirred for 2 hours at ambient temperature
  2. additionpoured onto ice water
  3. extractionThe aqueous phase is extracted twice with ethyl acetate
  4. washwashed four times with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated by evaporation in vacuo
  7. distillationThe residue remaining is distilled in vacuo
  8. custom110°-114° C.

Sources & evidence

ORD record
ord-def05e71a44547d59a0569a5268f9a91
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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