Dimethyl Sulfoxide → 4-Piperidineacetaldehyde, 1-(phenylmethyl)-

HRID 380497Notes

Reaction equation

HRID 380497 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][OH:26])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl.O>[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH:25]=[O:26])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27250292-(1-Benzylpiperidin-4-yl)ethanol

Product 1

HCID 100136024-Piperidineacetaldehyde, 1-(phenylmethyl)-Yield 100.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3 mL (34.4 mmol) of oxalyl chloride in 80 mL of CH2Cl2 at −78° C. was added a solution of 4.9 mL (68.8 mmol) of DMSO in 5 mL of CH2Cl2. After stirring for 10 min, a solution of 4 g (18.24 mmol) of 1-benzyl-4-(2-hydroxy-1-ethyl)piperidine (Acros Chemical) in 20 mL of CH2Cl2 was added dropwise. After 30 min, 12 mL (86.1 mmol) of Et3N was added and the reaction mixture was allowed to warm to rt over a period of 30 min. To the reaction mixture was added 100 mL of H2O and it was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaCl solution, and dried over MgSO4 and filtered. The filtrate was concentrated to give 4 g of the title compound.

Workup

  1. waitAfter 30 min
  2. extractionwas extracted with CH2Cl2
  3. washThe combined organic fractions were washed with sat'd NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c7bc376b886f44829d92a0ce025236d1
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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