N,N-diethyl-4-{[2-(4-morpholinyl)ethyl]amino}-3-nitrobenzamide → 3-amino-N,N-diethyl-4-{[2-(4-morpholinyl)ethyl]amino}benzamide

HRID 1796450Notes

Reaction equation

HRID 1796450 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:7]([N+:20]([O-])=O)[CH:6]=1)[CH3:2]>CO.[Pd]>[NH2:20][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[NH:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)[C:4]([N:3]([CH2:1][CH3:2])[CH2:24][CH3:25])=[O:23]

Participants

4

Reactant 1

HCID 22181356N,N-diethyl-4-{[2-(4-morpholinyl)ethyl]amino}-3-nitrobenzamide

Product 1

HCID 221813283-amino-N,N-diethyl-4-{[2-(4-morpholinyl)ethyl]amino}benzamideYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N,N-diethyl-4-{[2-(4-morpholinyl)ethyl]amino}-3-nitrobenzamide (1.10 g, 3.14 mmol) and 10% Pd/C in MeOH (50 mL) was hydrogenated for 2 hours at 40 psi. After the reaction was complete, the reaction mixture was filtered through diatomaceous earth. Removal of solvent provided the title compound (0.958 g, 95%) which was used without further purification. MS (ESI) (M+H)+=321.

Workup

  1. filtrationthe reaction mixture was filtered through diatomaceous earth
  2. customRemoval of solvent

Sources & evidence

ORD record
ord-5ccaa43d02424e02b024c01830f190c7
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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