Benzyl Bromide → 1-Benzyl-7-methylazepan-2-one

HRID 467476Notes

Reaction equation

HRID 467476 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[NH:10][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1.O>[CH2:12]([N:10]1[CH:4]([CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1372737-Methylcaprolactam

Product 1

HCID 584052661-Benzyl-7-methylazepan-2-one

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

Sodium hydride (95%, 1.74 g, 68.7 mmol, 1.15 equiv) was added to a solution of 7-methylazepan-2-one (2-2, 7.60 g, 59.8 mmol, 1 equiv) in THF (150 mL) at 0° C. and the resulting mixture was warmed to 23° C. and stirred for 20 h. Benzyl bromide (7.82 mL, 65.7 mmol, 1.10 equiv) was added followed by 2 drops of water, and the resulting mixture was stirred at 23° C. for 20 h. Excess sodium hydride was quenched carefully with water and the mixture was concentrated. The residue was partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (100% hexanes initially, grading to 100% EtOAc) to give 1-benzyl-7-methylazepan-2-one (2-3) as a colorless oil. LRMS m/z (M+H) 218.2 found, 218.2 required.

Workup

  1. stirringthe resulting mixture was stirred at 23° C. for 20 h
  2. customExcess sodium hydride was quenched carefully with water
  3. concentrationthe mixture was concentrated
  4. customThe residue was partitioned between water and dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (100% hexanes initially

Sources & evidence

ORD record
ord-f8f0810e016f4f9b894ecfe9c5de9ce5
Source dataset
uspto-grants-2014_01
Patent number
US08623863B2

Reaction notes

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