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

HRID 362933Notes

Reaction equation

HRID 362933 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[C:4]1[CH:5]=[CH:6][C:7]([N+:33]([O-])=O)=[C:8]([CH:32]=1)[C:9]([NH:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)=[O:10])[CH3:2]>O=[Pt]=O>[NH2:33][C:7]1[CH:6]=[CH:5][C:4]([N:3]([CH2:36][CH3:37])[CH2:1][CH3:2])=[CH:32][C:8]=1[C:9]([NH:11][CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:17][CH2:18]1)=[O:10]

Participants

3

Reactant 1

HCID 675967725-diethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Product 1

HCID 675958752-amino-5-diethylamino-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

Step 2): To a solution of 5-diethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (1.0 g, 1.99 mmol) was added PtO2 (30 mg). The solution was stirred under H2 atmosphere (3 kg/cm2) for 3 hours. The catalysts were filtered off and the filtrate was evaporated to give 2-amino-5-diethylamino-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide, 930 mg(100%): mp 161°-163° C.

Workup

  1. filtrationThe catalysts were filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-976ecc18339646d282c8747f0d7f3dd4
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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