HCID 19868639, compound → HCID 19868640, compound

HRID 330491Notes

Reaction equation

HRID 330491 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([O:15][C:16]1[CH:17]=[C:18]([CH:35]=[C:36]([O:38][C:39](=[O:41])[CH3:40])[CH:37]=1)[C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:28])=[O:20])(=[O:14])[CH3:13]>ClCCl>[C:27]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][N:21]1[C:19](=[O:20])[C:18]1[CH:17]=[C:16]([O:15][C:12](=[O:14])[CH3:13])[CH:37]=[C:36]([O:38][C:39](=[O:41])[CH3:40])[CH:35]=1)(=[O:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 19868639HCID 19868639, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 19868640HCID 19868640, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Add pyridinium chlorochromate (2.96 g) and 3Å, 1/16-inch molecular sieves (2.96 g) to a solution of 1-[3,5-bis(acetyloxy)benzoyl]-α-phenyl-2-piperidinemethanol (2.66 g) in dry dichloromethane (60 ml). Stir the resulting mixture at 23° C. for 4 hours. Filter the mixture through diatomaceous earth, and concentrate the filtrate. Chromatograph the residue over silica gel, and elute the column with 10% ethyl acetate in chloroform. Combine appropriate fractions, concentrate them, and crystallize the residue to obtain 2-benzoyl-1-[3,5-bis(acetyloxy)benzoyl]-piperidine, m.p. 77°-79° C. (from ether-pet. eth.).

Workup

  1. filtrationFilter the mixture through diatomaceous earth
  2. concentrationconcentrate the filtrate
  3. washChromatograph the residue over silica gel, and elute the column with 10% ethyl acetate in chloroform
  4. concentrationCombine appropriate fractions, concentrate them
  5. customcrystallize the residue

Sources & evidence

ORD record
ord-c323876ec09a4d7ea8cea9e227c45c80
Source dataset
uspto-grants-1990_01
Patent number
US04897391

Reaction notes

Loading…