N-(3,4-dichlorophenyl)-3-nitro-2-piperid-1-yl-5-trifluoromethylbenzamide → 3-amino-N-(3,4-dichlorophenyl)-2-piperid-1-yl-5-trifluoromethylbenzamide

HRID 550350Notes

Reaction equation

HRID 550350 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:30])[C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([N+:21]([O-])=O)[C:12]=2[N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H][H]>C1COCC1.[Ni]>[NH2:21][C:13]1[C:12]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:11]([CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=1)[C:10]([NH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:30]

Participants

5

Reactant 2

HCID 11854386N-(3,4-dichlorophenyl)-3-nitro-2-piperid-1-yl-5-trifluoromethylbenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 118543873-amino-N-(3,4-dichlorophenyl)-2-piperid-1-yl-5-trifluoromethylbenzamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3,4-dichlorophenyl)-3-nitro-2-piperid-1-yl-5-trifluoromethylbenzamide, Example 1 (4.15 g) in THF (80 ml), is added Raney nickel (2 g) under nitrogen. The reaction medium is hydrogenated at room temperature under a pressure of 45 bar. At the end of the reaction (stable absorption of hydrogen), the catalyst is removed and the medium is concentrated. 3.15 g of 3-amino-N-(3,4-dichlorophenyl)-2-piperid-1-yl-5-trifluoromethylbenzamide are obtained as a white solid.

Workup

  1. customis hydrogenated at room temperature under a pressure of 45 bar
  2. customthe catalyst is removed
  3. concentrationthe medium is concentrated

Sources & evidence

ORD record
ord-37b0814788a54c7a81a18fd1af91ac7d
Source dataset
uspto-grants-2011_05
Patent number
US07947675B2

Reaction notes

Loading…