Ammonium Chloride → 2,3-Diamino-6-(3-trifluoromethyl-piperidin-1-yl)benzonitrile

HRID 1258716Notes

Reaction equation

HRID 1258716 reaction equation
[NH2:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]([F:22])([F:21])[F:20])[CH2:14]2)[C:3]=1[C:4]#[N:5].[NH4+].[Cl-]>[Fe].CCO>[NH2:1][C:2]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]([F:22])([F:20])[F:21])[CH2:14]2)[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 679579752-Amino-3-nitro-6-(3-trifluoromethyl-piperidin-1-yl)benzonitrile

Product 1

HCID 679582702,3-Diamino-6-(3-trifluoromethyl-piperidin-1-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-3-nitro-6-(3-trifluoromethyl-piperidin-1-yl)benzonitrile (200 mg, 0.64 mmol), Fe (178 mg, 3.18 mmol), aqueous NH4Cl (5 mL) and EtOH (5 mL) was heated under Ar at 90° C. for 2 h. The mixture was thereafter basicified to pH ˜9-10 and filtered through celite and the celite pad was washed with EtOH and EtOAc. The organic layer was concentrated and the residue was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was washed with Et2O to give the sub-title compound.

Workup

  1. filtrationfiltered through celite
  2. washthe celite pad was washed with EtOH and EtOAc
  3. concentrationThe organic layer was concentrated
  4. extractionthe residue was extracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe residue was washed with Et2O

Sources & evidence

ORD record
ord-c6eaeed1973b47e6b1cb5934f0cd162f
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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