Cyclopropylamine → HCID 14651159, compound

HRID 232651Notes

Reaction equation

HRID 232651 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([F:14])=[C:12]([CH3:15])[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>CS(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]([CH3:15])[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 23359030HCID 23359030, compound

Product 1

HCID 14651159HCID 14651159, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To 2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-methyl-5-nitrotoluene (1.73 g) are added anhydrous dimethyl sulfoxide (18 ml), potassium fluoride (0.53 g) and cyclopropylamine (2.2 ml) and the mixture is stirred at 100° C. for 23 hours. After cooling, the mixture is poured into ice-water, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (dichloromethane: methanol=40:1) to give 3-(4-methyl-1-piperazinyl)-4-fluoro-2,5-dimethyl-6-nitro-N-cyclopropylaniline (1.65 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. customthe extract is dried
  4. distillationThe solvent is distilled off under reduced pressure
  5. customthe residue is purified by silica-gel column-chromatography (dichloromethane: methanol=40:1)

Sources & evidence

ORD record
ord-91f152fdeec24963a23baeb9b379d8f1
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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