Cyclopropylamine → N-cyclopropyl-2-ethyl-3-(4-methyl-1-piperazinyl)-4-fluoro-6-nitroaniline

HRID 1638687Notes

Reaction equation

HRID 1638687 reaction equation
[CH2:1]([C:3]1[C:4](F)=[C:5]([N+:17]([O-:19])=[O:18])[CH:6]=[C:7]([F:16])[C:8]=1[N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1)[CH3:2].[F-].[K+].[CH:23]1([NH2:26])[CH2:25][CH2:24]1>C(OCC)(=O)C>[CH:23]1([NH:26][C:4]2[C:5]([N+:17]([O-:19])=[O:18])=[CH:6][C:7]([F:16])=[C:8]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)[C:3]=2[CH2:1][CH3:2])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 522689Potassium FluorideHCID 198411213-Ethyl-2,5-difluoro-4-(4-methyl-1-piperazinyl)nitrobenzene

Product 1

HCID 19841167N-cyclopropyl-2-ethyl-3-(4-methyl-1-piperazinyl)-4-fluoro-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 3-ethyl-2,5-difluoro-4-(4-methyl-1-piperazinyl)nitrobenzene (1.12 g) are added potassium fluoride (0.24 g), N,N-dimethylsulfoxide (3.5 ml) and cyclopropylamine (0.4 ml), and the mixture is stirred at 80° to 85° C. for 1.5 hour. The reaction mixture is diluted with ethyl acetate, and the organic layer is washed with water and aqueous saturated sodium chloride and dried over magnesium sulfate and then concentrated under reduced pressure to give N-cyclopropyl-2-ethyl-3-(4-methyl-1-piperazinyl)-4-fluoro-6-nitroaniline (1.00 g), as viscous oil.

Workup

  1. washthe organic layer is washed with water and aqueous saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7898677a8f9f48b091f54af6d8a2384a
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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