1H-Imidazole-1-propanamine → (2-Fluoro-4-nitrophenyl)-(3-imidazol-1-ylpropyl)amine

HRID 988919Notes

Reaction equation

HRID 988919 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].[N:12]1([CH2:17][CH2:18][CH2:19][NH2:20])[CH:16]=[CH:15][N:14]=[CH:13]1>>[F:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH:20][CH2:19][CH2:18][CH2:17][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

3

Reactant 2

HCID 787361H-Imidazole-1-propanamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 18003903(2-Fluoro-4-nitrophenyl)-(3-imidazol-1-ylpropyl)amineYield 68.1%

Conditions

Temperature
96 °C

Procedure

Starting with 31.8 g (0.2 mol) of 1,2-difluoro-4-nitrobenzene and 37.5 g (0.3 mol) of 3-imidazol-1-ylpropylamine, and after purification by recrystallization from refluxing 96° C. ethanol, 36.0 g of orange-yellow crystals melting at 144° C. (Kofler) were obtained, the elemental analysis of which, calculated for C12H13N4O2F, was:

Workup

  1. customafter purification
  2. customby recrystallization

Sources & evidence

ORD record
ord-683554f75d7b4ccda1f521016a2017d4
Source dataset
uspto-grants-2003_10
Patent number
US06638321B1

Reaction notes

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