Dimethyl Sulfoxide → [4-(4-Benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanone

HRID 588235Notes

Reaction equation

HRID 588235 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][O:21][CH:20]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]([C:32]3[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:39])[OH:31])=[CH:26][CH:25]=2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC.[NH4+].[OH-]>C(Cl)Cl>[CH2:11]([N:18]1[CH2:23][CH2:22][O:21][CH:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([C:32]3[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:39])=[O:31])=[CH:26][CH:25]=2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 66653558HCID 66653558, compound

Product 1

HCID 66653880[4-(4-Benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanoneYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (0.46 mL, 5.4 mmol) in CH2Cl2 (20 mL), was added dropwise DMSO (0.94 mL, 13.2 mmol), at −78° C. Subsequently, a solution of [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanol (1.6 g, 4.1 mmol) in CH2Cl2 (30 mL) was added, dropwise, at −78° C. After the addition was complete the mixture was stirred for 30 min., at −78° C., and then Et3N (2.9 mL, 20.8 mmol) was added. After complete addition the mixture was allowed to warm to room temperature, overnight. Next, a 2M aqueous NH4OH solution (30 mL) was added, and the mixture extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanone (1.5 g), which was used as such in the next step.

Workup

  1. customat −78° C
  2. customat −78° C
  3. additionAfter the addition
  4. additionAfter complete addition the mixture
  5. temperatureto warm to room temperature, overnight
  6. extractionthe mixture extracted with CH2Cl2
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-453509416cc84b3a97ecd54cf91c3ad0
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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