Ethyl Acetate → 5-Amino-4-(methylamino)-2-(4-trifluoromethyl-piperidin-1-yl)benzonitrile

HRID 1258702Notes

Reaction equation

HRID 1258702 reaction equation
[CH3:1][NH:2][C:3]1[C:10]([N+:11]([O-])=O)=[CH:9][C:6]([C:7]#[N:8])=[C:5]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]([F:23])([F:22])[F:21])[CH2:16][CH2:15]2)[CH:4]=1.CCOC(C)=O>[Pd].CCO>[NH2:11][C:10]1[C:3]([NH:2][CH3:1])=[CH:4][C:5]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]([F:21])([F:22])[F:23])[CH2:16][CH2:15]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 679578224-(Methylamino)-5-nitro-2-(4-trifluoromethyl-piperidin-1-yl)benzonitrile

Product 1

HCID 679578515-Amino-4-(methylamino)-2-(4-trifluoromethyl-piperidin-1-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

H2 (1 atm) was passed through a mixture of 4-(methylamino)-5-nitro-2-(4-trifluoromethyl-piperidin-1-yl)benzonitrile (204 mg, 0.62 mmol), Pd/C (66 mg, 0.062 mmol), EtOAc (10 mL) and EtOH (10 mL) at rt for 1 h. The mixture was filtered through celite and concentrated. Crystallization from Et2O/PE gave the sub-title compound.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated
  3. customCrystallization from Et2O/PE

Sources & evidence

ORD record
ord-981869cbd2ee433c81a76f87ba1dfe63
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

Loading…