Dimethyl Sulfoxide → HCID 13925233, compound

HRID 501214Notes

Reaction equation

HRID 501214 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])[CH:20]([OH:32])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])[C:20](=[O:32])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13925231HCID 13925231, compound

Product 1

HCID 13925233HCID 13925233, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of oxalyl chloride (0.839 g, 6.73 mmol) in dry DCM (5 mL) was added dimethylsulfoxide (1.05 g, 13.46 mmol) dropwise. The mixture was stirred for 10 min at −78° C., 1-benzyl-4-(2-methoxyphenyl)piperidin-3-ol (1.0 g, 3.367 mmol) in DCM (10 mL) was added and stirring continued for a further 20 min at −78° C. Triethylamine (3.3 ml, 23.56 mmol) was added, the reaction mixture was stirred for 15 min at −78° C., warmed to room temperature and diluted with water. The organic layer washed with 2N HCl (50 mL), 10% aqueous sodium bicarbonate solution, brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 1-benzyl-4-(2-methoxyphenyl)piperidin-3-one (0.7 g, 70%) which was used in the next step without further purification. 1H NMR (200 MHz, CDCl3): δ 2.72 (m, 2H) 2.91-3.045 (m, 2H), 3.71 (m, 2H), 3.80 (s, 2H), 6.87-6.99 (m, 2H), 7.12 (dd, J=7.5, 1.7 Hz, 1H), 7.18-7.45 (m, 6H); m/e=295 (M+1).

Workup

  1. stirringstirring
  2. waitcontinued for a further 20 min at −78° C
  3. stirringthe reaction mixture was stirred for 15 min at −78° C.
  4. temperaturewarmed to room temperature
  5. washThe organic layer washed with 2N HCl (50 mL), 10% aqueous sodium bicarbonate solution, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1098f9fe1eb41f1a26d79fedc3b088f
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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