Dimethyl Sulfoxide → 4-(Dibenzylamino)cyclohexan-1-one

HRID 1963903Notes

Reaction equation

HRID 1963903 reaction equation
CS(C)=O.[CH2:5]([N:12]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCN(CC)CC>C(Cl)Cl>[CH2:20]([N:12]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:13]1[CH2:14][CH2:15][C:16](=[O:19])[CH2:17][CH2:18]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 22484911trans-4-(Dibenzylamino)cyclohexanol

Product 1

HCID 220099024-(Dibenzylamino)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalylic acid (2.03 mL, 20.31 mmol) in DCM (80 mL) at −60° C. was added dropwise DMSO (3.46 mL, 48.8 mmol). After stirring for 5 min, a solution of 4-(dibenzylamino)cyclohexanol (6 g, 20.31 mmol) in DCM (40 mL) was added slowly. The mixture was stirred for 15 min and NEt3 (14.3 mL, 103 mmol) was added slowly. After stirring for 15 min the ice bath was removed and the mixture was stirred for additional 16 hr. The mixture was diluted with water (100 mL). The separated organic layer was washed with brine (1ט75 mL), dried over Na2SO4, filtered off and concentrated in vacuo. The resulting residue was purified by column chromatography [SiO2, 120 g, EtOAc/hexane= 10/90 to 50/50] providing 4-(dibenzylamino)cyclohexanone as a white solid. Yield: 5.5 g. LCMS (m/z): 294.1 [M+H]+; Retention time=0.58 min.

Workup

  1. stirringThe mixture was stirred for 15 min
  2. customwas removed
  3. stirringthe mixture was stirred for additional 16 hr
  4. additionThe mixture was diluted with water (100 mL)
  5. washThe separated organic layer was washed with brine (1ט75 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered off
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by column chromatography [SiO2, 120 g, EtOAc/hexane= 10/90 to 50/50]

Sources & evidence

ORD record
ord-47ca27d2fccf4510980e3308e9bbe2d1
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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