5-dimethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide → 2-amino-5-dimethylamino-N-[(1-diphenylmethylpiperidin-4-yl)-methyl]benzamide

HRID 362898Notes

Reaction equation

HRID 362898 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1[CH:4]=[CH:5][C:6]([N+:32]([O-])=O)=[C:7]([CH:31]=1)[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:9].[H][H]>CO.[Ni]>[NH2:32][C:6]1[CH:5]=[CH:4][C:3]([N:2]([CH3:35])[CH3:1])=[CH:31][C:7]=1[C:8]([NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:17]1)=[O:9]

Participants

5

Reactant 2

HCID 542091215-dimethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 675952632-amino-5-dimethylamino-N-[(1-diphenylmethylpiperidin-4-yl)-methyl]benzamideYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Step 2): A mixture of 5-dimethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)-methyl]benzamide (2.4 g, 5 mmol) and Raney Ni in methanol (50 ml) was hydrogenated at room temperature under stirring under 50 psi hydrogen pressure for 2 hours and then filtered. The filtrate was concentrated to give 2-amino-5-dimethylamino-N-[(1-diphenylmethylpiperidin-4-yl)-methyl]benzamide (2.2 g, 100%).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8a9b61d1c94149108883517e985e0966
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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