Cyclopropylamine → HCID 23359026, compound

HRID 232667Notes

Reaction equation

HRID 232667 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([F:14])=[C:12]([Cl:15])[C:11]([N+:16]([O-:18])=[O:17])=[C:10](F)[C:9]=2[CH3:20])[CH2:4][CH2:3]1.[F-].[K+].[CH:23]1([NH2:26])[CH2:25][CH2:24]1>CN(C)C=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([CH3:20])=[C:10]([C:11]([N+:16]([O-:18])=[O:17])=[C:12]([Cl:15])[C:13]=2[F:14])[NH:26][CH:23]2[CH2:25][CH2:24]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 522689Potassium FluorideHCID 23359031HCID 23359031, compound

Product 1

HCID 23359026HCID 23359026, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To the thus obtained 2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-chloro-5-nitrotoluene (0.13 g) are added anhydrous dimethylformamide (2 ml), potassium fluoride (37 mg) and cyclopropylamine (0.15 ml) and the mixture is stirred at 100° C. for 3 hours. After cooling, the reaction mixture is poured into ice-water, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure and purified by silica-gel column-chromatography (eluent; dichloromethane: methanol=10:1) to give 3-(4-methyl-1-piperazinyl)-4-fluoro-5-chloro-2-methyl-6-nitro-N-cyclopropylaniline (0.14 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. customthe extract is dried
  4. distillationThe solvent is distilled off under reduced pressure
  5. custompurified by silica-gel column-chromatography (eluent; dichloromethane: methanol=10:1)

Sources & evidence

ORD record
ord-c6076633e043445887513dfa91aad75a
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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