Phenethylamine → N,N-diethyl-3-nitro-4-[(2-phenylethyl)amino]benzamide

HRID 1796459Notes

Reaction equation

HRID 1796459 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[C:18]1([CH2:24][CH2:25][NH2:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCO>[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:26][CH2:25][CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 22181444N,N-diethyl-4-fluoro-3-nitrobenzamide

Product 1

HCID 22181379N,N-diethyl-3-nitro-4-[(2-phenylethyl)amino]benzamideYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Following general procedure 2B: A mixture of N,N-diethyl-4-fluoro-3-nitrobenzamide (0.125 g, 0.521 mmol), 2-phenylethanamine (0.065 mL, 0.521 mmol) in 80% aq. EtOH (3 mL) was heated at 85° C. for 4 hours. Usual work-up provided the title compound (0.170 g, 96%) which was used without further purification. MS (ESI) (M+H)+=342.

Sources & evidence

ORD record
ord-4268a9bef4784ee2b78db5e7768148c1
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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