Potassium Carbonate → HCID 16667330, compound

HRID 1927608Notes

Reaction equation

HRID 1927608 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][CH:15]([CH:18]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([NH:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13]1)#[N:2].C(N[C:33](=[O:47])[CH:34]([C:41]1C=CC=C[CH:42]=1)[CH:35]1CCNC[CH2:36]1)C.FC1C=CC([N+]([O-])=O)=CC=1C#N.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]([C:3]1[CH:8]=[C:7]([NH:9][C:33](=[O:47])[CH:34]([CH2:41][CH3:42])[CH2:35][CH3:36])[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][CH:15]([CH:18]([C:19](=[O:20])[NH:21][CH2:22][CH3:23])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:14][CH2:13]1)#[N:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 69304313HCID 69304313, compoundHCID 69304327HCID 69304327, compound

Product 1

HCID 16667330HCID 16667330, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-[1-(2-Cyano-4-nitro-phenyl)-piperidin-4-yl]-N-ethyl-2-phenyl-acetamide. To a solution of N-ethyl-2-phenyl-2-piperidin-4-yl-acetamide (500 mg, 2 mmol) and 2-fluoro-5-nitro-benzonitrile (337 mg, 2.03 mmol) in DMF was added K2CO3 (840 mg, 6.1 mmol). The solution was heated to 80° C. for 16 h. After cooling to rt, H2O and 3:1 EtOAc/hexanes were added. The organic portion was washed three times with H2O and once with brine, dried (Na2SO4) and concentrated to provide the title compound (yellow powder, 686 mg, 86%).

Workup

  1. temperatureAfter cooling to rt
  2. washThe organic portion was washed three times with H2O
  3. dry with materialonce with brine, dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9c41ec5506e74e9a832a33d801709caa
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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