Benzhydrol → HCID 23025374, compound

HRID 1437625Notes

Reaction equation

HRID 1437625 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[CH:23](O)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(=O)C.[Na+]>ClCCl.O>[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH:6]([CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 7037BenzhydrolHCID 65367Trimethylsilyl triflateHCID 122563N-Acetyl-4-piperidoneHCID 517045Sodium Acetate

Product 1

HCID 23025374HCID 23025374, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-Acetyl-4-piperidinone (77 g) was dissolved in dichloromethane (300 ml), and trimethylsilyltrifluoromethanesulfonate (200 ml) and benzhydrol (92 g) were added thereto with stirring under ice-cooling. The mixture was allowed to stand at room temperature overnight, and then water (500 ml) and sodium acetate (50 g) were added thereto and the reaction mixture was vigorously stirred. The dichloromethane layer was preparatively separated, washed with an aqueous sodium bicarbonate solution, dried, and then the solvent was evaporated under reduced pressure. The residue was treated with ethyl ether to obtain 1-acetyl-3-benzhydryl-4-piperidinone as colorless crystals (132.6 g, 86%).

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was vigorously stirred
  3. customThe dichloromethane layer was preparatively separated
  4. washwashed with an aqueous sodium bicarbonate solution
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. additionThe residue was treated with ethyl ether

Sources & evidence

ORD record
ord-73b4537f7d2542de8c39ff0afeb0f4df
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

Loading…