Dimethyl Sulfoxide → HCID 18930351, compound

HRID 266101Notes

Reaction equation

HRID 266101 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([CH:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)[OH:26])[CH2:21][CH2:20]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[S:28]1[CH:29]=[CH:30][CH:31]=[C:27]1[C:25]([CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:20][CH2:21]1)=[O:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18930330HCID 18930330, compound

Product 1

HCID 18930351HCID 18930351, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dissolve oxalyl chloride (1.23 g, 9.67 mmol) in methylene chloride (100 mL), place under an argon atmosphere and cool to -78° C. Add dimethylsulfoxide (1.43 mL) and stir for 15 minutes. Add, by dropwise addition, a solution of α-[1-(2-phenylethyl)-4-piperidinyl]-2-thiophenemethanol (2.43 g, 8.06 mmol) in methylene chloride (100 mL). Stir at -78° C. for 30 minutes, then add triethylamine (6.07 mL). Stir at -78° C. for 30 minutes, remove the ice bath and allow to warm to room temperature. Evaporate the solvent in vacuo and partition between methylene chloride and water. Separate the organic phase and extract the aqueous phase with methylene chloride. Combine the organic phases, wash with water and dry (MgSO4). Evaporate the solvent in vacuo and recrystallize (isopropanol) to give the title compound as a white crystalline solid; mp 77°-79° C.

Workup

  1. additionAdd, by dropwise addition
  2. stirringStir at -78° C. for 30 minutes
  3. customremove the ice bath
  4. temperatureto warm to room temperature
  5. customEvaporate the solvent in vacuo
  6. custompartition between methylene chloride and water
  7. customSeparate the organic phase
  8. extractionextract the aqueous phase with methylene chloride
  9. washwash with water
  10. dry with materialdry (MgSO4)
  11. customEvaporate the solvent in vacuo
  12. customrecrystallize (isopropanol)

Sources & evidence

ORD record
ord-5d33c0db259844288ccb333e5b24ba5a
Source dataset
uspto-grants-1997_07
Patent number
US05650416

Reaction notes

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