Dimethyl Sulfoxide → Benzyl 4-(2-oxoethyl)piperidine-1-carboxylate

HRID 129510Notes

Reaction equation

HRID 129510 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH2:28][OH:29])[CH2:23][CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH:28]=[O:29])[CH2:23][CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13971210Benzyl 4-(2-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 22278282Benzyl 4-(2-oxoethyl)piperidine-1-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

159 g of oxalic acid chloride was dissolved in one liter of dichloromethane, in to which 195.8 g of dimethyl sulfoxide was dropped at -67° C., followed by agitation for 30 minutes. Thereafter, 200 ml of dichloromethane dissolving 66 g of 1-benzyloxycarbonyl-4-(2-hydroxyethyl)-piperidine was dropped at -67° C. Subsequently, 380 g of triethylamine was dropped at -67° C., followed by agitation for about 1 hour. After removal of the solvent by distillation, ethyl acetate was added and insoluble matters were removed by filtration, and the resultant filtrate was washed with water and dried with anhydrous magnesium sulfate, followed by filtration and removal of the solvent by distillation. The resultant residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:hexane=20:80) to obtain 55.0 g of the captioned compound (yield 84%).

Workup

  1. additionwas dropped at -67° C.
  2. waitfollowed by agitation for about 1 hour
  3. customAfter removal of the solvent
  4. distillationby distillation, ethyl acetate
  5. additionwas added
  6. custominsoluble matters were removed by filtration
  7. washthe resultant filtrate was washed with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. filtrationfollowed by filtration and removal of the solvent by distillation

Sources & evidence

ORD record
ord-cfd2ee12d49345fc81f5bc852179040d
Source dataset
uspto-grants-1995_11
Patent number
US05468740

Reaction notes

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