Benzyl Bromide → 3-Benzyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 35080

Reaction equation

HRID 35080 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:16][CH:14]([CH2:15]2)[C:13](=[O:17])[NH:12][C:11]3=[O:18])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([N:12]1[C:13](=[O:17])[CH:14]2[CH2:15][C:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)([CH2:16]2)[C:11]1=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 148726291-(4-Nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 148726333-Benzyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4.92 g of 1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione are dissolved in 70 ml of dimethylformamide and, under a nitrogen atmosphere, 1.2 g of sodium hydride (pract. Fluka) are added. After stirring for 30 minutes at room temperature, the mixture is cooled to 0°, and a solution of 4.5 g of benzyl bromide in 10 ml of dimethylformamide is added dropwise thereto. After the addition is complete, the mixture is stirred at room temperature for 4 hours. The excess sodium hydride is destroyed by the addition of methanol, and concentration by evaporation is effected in vacuo. The residue is taken up in ethyl acetate and washed with water and aqueous sodium chloride solution. After drying over magnesium sulphate, the mixture is filtered and concentrated by evaporation. Melting point 150°-152° (from ether).

Workup

  1. temperaturethe mixture is cooled to 0°
  2. additionAfter the addition
  3. stirringthe mixture is stirred at room temperature for 4 hours
  4. customThe excess sodium hydride is destroyed by the addition of methanol, and concentration by evaporation
  5. washwashed with water and aqueous sodium chloride solution
  6. dry with materialAfter drying over magnesium sulphate
  7. filtrationthe mixture is filtered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c7da1d78a12a40c8a926c822e55f791f
Source dataset
uspto-grants-1988_08
Patent number
US04764640

Linked notes

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