Dimethyl Sulfoxide → HCID 10104772, compound

HRID 538681Notes

Reaction equation

HRID 538681 reaction equation
CS(C)=O.C(Cl)(C(Cl)=O)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH2:24][CH2:25][OH:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[CH2:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH2:24][CH:25]=[O:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 102425512-(1-Benzylpiperidin-2-yl)ethan-1-ol

Product 1

HCID 10104772HCID 10104772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of DMSO (5.84 mL, 82.2 mmol) in dry DCM (220 mL) was added (COCl)2 (3.55 mL, 41.1 mmol) at −78° C. and the mixture stirred at same temperature for 20 minutes. A solution of compound 49 (6 g, 27.4 mmol) in DCM (30 mL) was then added slowly and the reaction mixture was stirred at −78° C. for 1 hour. TEA (13.8 mL, 137 mmol) was added at −78° C. and the reaction mixture was stirred and allowed to come to rt. The reaction mixture was diluted with DCM and the organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated to provide sticky compound 50.

Workup

  1. stirringthe reaction mixture was stirred at −78° C. for 1 hour
  2. stirringthe reaction mixture was stirred
  3. customto come to rt
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-915e4ff0ff5e4bcb83f002c4e5a28fcc
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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