HCID 54562765, compound → HCID 53633357, compound

HRID 362921Notes

Reaction equation

HRID 362921 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1[CH:30]=[CH:29][C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:8])=[C:5]([N+:31]([O-])=O)[CH:4]=1>[Ni].CCO>[NH2:31][C:5]1[CH:4]=[C:3]([N:2]([CH3:34])[CH3:1])[CH:30]=[CH:29][C:6]=1[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:11]1)=[O:8]

Participants

4

Reactant 1

HCID 54562765HCID 54562765, compound

Product 1

HCID 53633357HCID 53633357, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Step 4): The mixture of 4-dimethylamino-2-nitro-N-(1-diphenylmethylpiperidin-4-yl)-bezamide (1.60 g, 3.5 mmol) and Raney Nickel in EtOH (75 ml) was stirred under H2 at room temperature for 4 hours. The mixture was filtered, and the filtrate was concentrated under vacuum. The residue was purified with chromatography on silica gel (30-50% AcOEt in hexane) and recrystallized from diisopropyl ether to obtain 2-amino-4-dimethylamino-N-(1-diphenylmethyl-piperidin-4-yl)benzamide 1.18 g (79%): mp 118° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified with chromatography on silica gel (30-50% AcOEt in hexane)
  4. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ecd5ac60715c4df1900638f94a189d2f
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

Loading…