Potassium Carbonate → N-{1-(Thiomorpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

HRID 876326

Reaction equation

HRID 876326 reaction equation
[C:1]1([C:7]([NH:9][CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:26]([O:28]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:11]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:38]1[CH2:43][CH2:42][S:41][CH2:40][CH2:39]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:38]1([C:26]([N:12]2[CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][CH:17]=3)[CH2:15][CH:10]([NH:9][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:8])[CH2:11]2)=[O:28])[CH2:43][CH2:42][S:41][CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 667014674-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 66761420N-{1-(Thiomorpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80 mg (0.16 mmol) of 4-nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate were initially charged in 1.7 ml of DMF, and 48 mg (0.47 mmol) of thiomorpholine and 22 mg (0.16 mmol) of potassium carbonate were added. The mixture was reacted in a microwave (Emrys Optimizer) at 150° C. for 15 min. The crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 45 mg (60% of theory)

Workup

  1. customThe mixture was reacted in a microwave (Emrys Optimizer) at 150° C. for 15 min
  2. customThe crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-09a5ed7cf9ff4463b5a067e16816f9d1
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Linked notes

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