Dimethyl Sulfoxide → HCID 86707842, compound

HRID 1844660Notes

Reaction equation

HRID 1844660 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][OH:21])[CH2:15][CH2:14]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][O:12][N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20]=[O:21])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68299260HCID 68299260, compound

Product 1

HCID 86707842HCID 86707842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cooled (−78° C.) solution of oxalyl chloride (23.8 g, 189 mmol) in 100 ml of methylene chloride, DMSO (29.6 g, 380 mmol) was added slowly and the mixture was stirred for 0.5 h at the same temperature. Then, a solution of 2-(1-methoxy-piperidin-4-yl)-ethanol (12 g, 75 mmol) in 50 ml of methylene chloride was added. After stirring for 30 minutes, triethylamine (44 g, 430 mmol) was added to the mixture. After the addition, the reaction mixture was warmed to room temperature and diluted with methylene chloride. The organic solution was washed with water and aqueous NaHCO3. The organic layers was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel. Yield: 11.5 g of (1-methoxy-piperidin-4-yl)-acetaldehyde as an oil.

Workup

  1. additionwas added slowly
  2. stirringAfter stirring for 30 minutes
  3. additionAfter the addition
  4. washThe organic solution was washed with water and aqueous NaHCO3
  5. dry with materialThe organic layers was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-409fbcd8ba7f4eed98d86c27a7c3908f
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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