Benzyl Bromide → 1-Benzyl-hexahydro-4H-azepin-4-one

HRID 239169Notes

Reaction equation

HRID 239169 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH:10]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[CH2:1]([N:10]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22021728Azepan-4-one hydrochloride

Product 1

HCID 15143501-Benzyl-hexahydro-4H-azepin-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

6 mL benzyl bromide was added to 5 g azepane-4-one hydrochloride and 18.5 g potassium carbonate in 50 mL THF and 25 mL water. The mixture was stirred 5 h at 50° C., evaporated, diluted with water and extracted with ethyl acetate. The organic layer was evaporated. The residue was purified by chromatographie on silica gel (petrolether/ethyl acetate:8/2) to give 5 g of the desired product. Rf: 0.40 (hexane/ethyl acetate=1/1), (M+H)+=204

Workup

  1. customevaporated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was evaporated
  5. customThe residue was purified by chromatographie on silica gel (petrolether/ethyl acetate:8/2)

Sources & evidence

ORD record
ord-d929d278a21d45dca3cdf37031c925dd
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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