Morpholine → 2-Benzyl-2-(dimethylamino)-1-(4-(morpholin-4-yl)phenyl)butan-1-one

HRID 1780031Notes

Reaction equation

HRID 1780031 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[C:9]([N:19]([CH3:21])[CH3:20])([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH3:11])=[CH:4][CH:3]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH2:12]([C:9]([N:19]([CH3:21])[CH3:20])([CH2:10][CH3:11])[C:8]([C:5]1[CH:6]=[CH:7][C:2]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:3][CH:4]=1)=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 193605992-Benzyl-2-(dimethylamino)-1-(4-fluorophenyl)butan-1-one

Product 1

HCID 861712-Benzyl-2-(dimethylamino)-1-(4-(morpholin-4-yl)phenyl)butan-1-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

608.7 g (2.03 mol) of 1-(4-fluorophenyl)-2-dimethylamino-2-benzyl-butan-1-one (Example 1, B), 354.2 g (4.06 mol) of morpholine, 562 g (4.06 mol) of K2CO3 and 2000 ml of dimethylsulfoxide are heated at 160° for 12 hours, with stirring. After this time, a sample no longer shows any starting ketone in a thin-layer chromatogram. The reaction solution is cooled to room temperature, poured onto ice and extracted with methylene chloride. The organic phase is dried over MgSO4, filtered and evaporated. The oily residue crystallizes from ethanol. The product melts at 111°-119°.

Workup

  1. additionpoured onto ice
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe oily residue crystallizes from ethanol

Sources & evidence

ORD record
ord-b55a29a208b14930af65ade5e98b5cbb
Source dataset
uspto-grants-1997_05
Patent number
US05629356

Reaction notes

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