Dimethyl Sulfoxide → 1-(4-Methylbenzyl)piperidin-4-one

HRID 2249343Notes

Reaction equation

HRID 2249343 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)=[CH:14][CH:13]=1.C(N(CC)CC)C.[Cl-].[NH4+]>C(Cl)Cl>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH2:22]2)=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 7914821-(4-Methylbenzyl)piperidin-4-ol

Product 1

HCID 119595411-(4-Methylbenzyl)piperidin-4-oneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2.8 mL (32 mmol) of oxalyl chloride in 75 mL of CH2Cl2 at −78° C. was added 4.6 mL (64 mmol) of DMSO. To this mixture was added 5.3 g (26 mmol) of 1-(4-methylbenzyl)-4-piperidinol 123 in 10 mL of CH2Cl2, and the mixture was stirred 5 min in the cold. The mixture was quenched with 18 mL (129 mmol) of triethylamine and allowed to come to room temperature, and saturated aqueous ammonium chloride was added. The organic phase was washed with water and brine, dried, and evaporated to give 4.27 g (81%) of 1-(4-methylbenzyl)-4-piperidinone (124), which was used as is without further purification. GC/MS showed 100% purity with a molecular ion of 203.

Workup

  1. customto come to room temperature
  2. washThe organic phase was washed with water and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-5a2b112e5fd44e89ac25b917bbdea207
Source dataset
uspto-grants-2008_01
Patent number
USRE039991E1

Reaction notes

Loading…