Dimethyl Sulfoxide → 4-(4-Methyl-3-oxo-piperazin-1-yl)-cyclohexan-1-one

HRID 1672129Notes

Reaction equation

HRID 1672129 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[C:20](=[O:25])[CH2:19]2)[CH2:14][CH2:13]1.C(N(CC)CC)C>ClCCl.O>[CH3:24][N:21]1[CH2:22][CH2:23][N:18]([CH:15]2[CH2:14][CH2:13][C:12](=[O:11])[CH2:17][CH2:16]2)[CH2:19][C:20]1=[O:25]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178481021HCID 178481021, compound

Product 1

HCID 591581724-(4-Methyl-3-oxo-piperazin-1-yl)-cyclohexan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

0.55 ml dimethylsulphoxide in 2 ml dichloromethane are added dropwise to 0.46 ml oxalyl chloride in 10 ml dichloromethane within two minutes at −60° C. After 5 minutes 1.0 g (trans)-1-hydroxy-4-(4-methyl-3-oxo-piperazin-1-yl)-cyclohexane in 8 ml dichloromethane are added within 5 min. After 20 minutes 3.3 ml triethylamine are added and the mixture is stirred for 70 minutes at ambient temperature. 15 ml of water are added and the mixture is extracted with dichloromethane. After evaporation of the solvent the residue contains the product.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. customAfter evaporation of the solvent the residue

Sources & evidence

ORD record
ord-99616da673f94b339aca37818138ee33
Source dataset
uspto-grants-2011_08
Patent number
US07998949B2

Reaction notes

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