N,N-diethyl-3-nitro-4-{[2-(1-piperidinyl)ethyl]amino}benzamide → 3-amino-N,N-diethyl-4-{[2-(1-piperidinyl)ethyl]amino}benzamide

HRID 1796462Notes

Reaction equation

HRID 1796462 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][CH2:17][CH2:16][CH2:15]2)=[C:7]([N+:20]([O-])=O)[CH:6]=1)[CH3:2]>CCOC(C)=O.[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[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:4]([N:3]([CH2:24][CH3:25])[CH2:1][CH3:2])=[O:23]

Participants

4

Reactant 1

HCID 22181369N,N-diethyl-3-nitro-4-{[2-(1-piperidinyl)ethyl]amino}benzamide

Product 1

HCID 221813403-amino-N,N-diethyl-4-{[2-(1-piperidinyl)ethyl]amino}benzamideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure 2C: A mixture of N,N-diethyl-3-nitro-4-{[2-(1-piperidinyl)ethyl]amino}benzamide (0.800 g, 2.30 mmol) and 10% Pd/C in EtOAc (30 mL) was hydrogenated for 24 hours at 30 psi. Usual work-up provided the title compound (0.724 g, 99%) which was used without further purification.

Sources & evidence

ORD record
ord-4315e31698344dec8413862389243559
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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