Dimethyl Sulfoxide → N-(3,4-Dimethylisoxazol-5-yl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxamide

HRID 2263331Notes

Reaction equation

HRID 2263331 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][C:9](=[O:16])OCC(Cl)(Cl)Cl)[O:4][N:3]=1.[C:17]1([C:23]2[O:27][C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:25][N:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][C:9]([N:31]2[CH2:30][CH2:29][CH:28]([C:26]3[O:27][C:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:24][N:25]=3)[CH2:33][CH2:32]2)=[O:16])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27611504-(5-Phenyl-1,3,4-oxadiazol-2-yl)piperidineHCID 862452572,2,2-Trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate

Product 1

HCID 59594508N-(3,4-Dimethylisoxazol-5-yl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxamideYield 37.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl (3,4-dimethylisoxazol-5-yl)carbamate (293 mg, 1.02 mmol), 4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine (234 mg, 1.02 mmol), diisopropylethylamine (0.387 ml, 2.05 mmol) and dimethyl sulfoxide (4 ml) was stirred at 70° C. for 12 hours, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to give 142 mg (37.9%) of the desired product as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-be87a3b985334a2b9dfd0ea492cf4bad
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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