Potassium Carbonate → 4-(Methylamino)-5-nitro-2-(4-trifluoromethyl-piperidin-1-yl)benzonitrile

HRID 1258701Notes

Reaction equation

HRID 1258701 reaction equation
Cl[C:2]1[CH:9]=[C:8]([NH:10][CH3:11])[C:7]([N+:12]([O-:14])=[O:13])=[CH:6][C:3]=1[C:4]#[N:5].[F:15][C:16]([F:24])([F:23])[CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+].[NH4+].[OH-]>CN(C=O)C>[CH3:11][NH:10][C:8]1[C:7]([N+:12]([O-:14])=[O:13])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([N:20]2[CH2:21][CH2:22][CH:17]([C:16]([F:24])([F:23])[F:15])[CH2:18][CH2:19]2)[CH:9]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 1364694-(Trifluoromethyl)piperidineHCID 679576272-Chloro-4-(methylamino)-5-nitrobenzonitrile

Product 1

HCID 679578224-(Methylamino)-5-nitro-2-(4-trifluoromethyl-piperidin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-4-(methylamino)-5-nitrobenzonitrile (3.07 g, 14.5 mmol), 4-trifluoromethylpiperidine (3.33 g, 21.7 mmol), K2CO3 (5.01 g, 36.2 mmol) and DMF (16 mL) was heated at 60° C. for 6 h under Ar atmosphere. The mixture was poured into aqueous NH4OH and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. Crystallization from EtOAc/PE gave the sub-title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customCrystallization from EtOAc/PE

Sources & evidence

ORD record
ord-b49684c80e684482b844da77f2e73f83
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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