Dimethyl Sulfoxide → HCID 69663068, compound

HRID 2212099Notes

Reaction equation

HRID 2212099 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([S:17]([C:20]([CH3:32])([CH3:31])[CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH:26]([OH:30])[CH2:25]2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([S:17]([C:20]([CH3:32])([CH3:31])[CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]2)(=[O:18])=[O:19])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 696627361-(4-Benzenesulfonyl-4-methylpentyl)-3-hydroxypiperidine

Product 1

HCID 69663068HCID 69663068, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Dimethylsulphoxide (1.2 ml, 16.6 mmol) was added to a solution of oxalyl chloride (1.5 ml, 16.6 mmol) in dichloromethane (200 ml) at −78° C. and stirred for 15 minutes. 1-(4-Benzenesulfonyl-4-methylpentyl)-3-hydroxypiperidine (3.5 g, 11.0 mmol) in dichloromethane (50 ml) was added and the reaction stirred at −20° C. for 15 minutes. Triethylamine (4.6 ml, 33 mmol) was added and the reaction stirred for 90 minutes, warming slowly to room temperature. The mixture was diluted with dichloromethane and washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 5% methanol/dichloromethane to give the title compound (2.8 g, 80%).

Workup

  1. stirringthe reaction stirred at −20° C. for 15 minutes
  2. stirringthe reaction stirred for 90 minutes
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-e51ba534182e416b931cfafbcfacd5cd
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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