Benzyl Bromide → HCID 22273796, compound

HRID 1064381Notes

Reaction equation

HRID 1064381 reaction equation
[OH:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([C:14]([N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[O:15])[CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CCO>[CH2:34]([O:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([C:14]([N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:18][CH2:17]3)=[O:15])[CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide3×HCID 11430Potassium CarbonateHCID 22273744HCID 22273744, compound

Product 1

HCID 22273796HCID 22273796, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

600 mg (0.00165 mol) of (±)-1-hydroxy-7-[(4-phenylpiperidin-1-yl)carbonyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one were dissolved in 100 mL of abs. EtOH under a nitrogen atmosphere, then 228 mg (0.00165 mol) of anhydrous K2CO3 and a catalytic amount of KI were added, followed by 0.216 mL (0.0018 mol) of benzylbromide. The reaction mixture was stirred 3 h at room temperature, then 0.216 mL of benzylbromide were added and the stirring continued overnight. Further 0.216 mL of benzylbromide was added and the reaction stirred overnight. The solvent was then evaporated, the residue was taken up in water, brought to pH 1 with 1N HCl and extracted with AcOEt. The organic phase was dried and the solvent was removed in vacuo, the resulting crude product was purified by flash chromatography, eluting with a mixture Et2O/Hexane 8:2 respectively, yielding 595 mg of the title compound.

Workup

  1. customthe stirring continued overnight
  2. stirringthe reaction stirred overnight
  3. customThe solvent was then evaporated
  4. extractionextracted with AcOEt
  5. customThe organic phase was dried
  6. customthe solvent was removed in vacuo
  7. customthe resulting crude product was purified by flash chromatography
  8. washeluting with a mixture Et2O/Hexane 8:2 respectively

Sources & evidence

ORD record
ord-b17f43ecdbfa40a8a37e8bf53f9a2627
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

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