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

HRID 2351903Notes

Reaction equation

[F:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]2)=[C:4]([CH3:12])[C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[F-].[K+].[CH:26]1([NH2:29])[CH2:28][CH2:27]1>CS(C)=O>[CH:26]1([NH:29][C:5]2[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]([F:1])=[C:3]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:4]=2[CH3:12])[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 60 °C

Procedure

To 3,6-difluoro-2-(4-ethoxycarbonyl-1-piperazinyl)-5-nitrotoluene (7.1 g) are added anhydrous dimethylsulfoxide (23 ml), potassium fluoride (2.0 g) and cyclopropylamine (1.5 g), and the mixture is heated at 60° C. for 6 hours. The reaction mixture is poured into ice water, and extracted with dichloromethane. The solvent is distilled off and the residue is recrystallized from ethanol to give N-cyclopropyl-2-methyl-3-(4-ethoxycarbonyl-1-piperazinyl)-4-fluoro-6-nitroaniline (7.4 g), as orange red prisms, m.p. 97°-98° C.

Workup

extractionextracted with dichloromethane
distillationThe solvent is distilled off
customthe residue is recrystallized from ethanol

Sources & evidence

ORD record: ord-3a434ef697d441299017dadf58c089de
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04874764

Reaction notes

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