4-(4-Methylpiperazin-1-yl)aniline → HCID 68693656, compound

HRID 2236619Notes

Reaction equation

HRID 2236619 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.O/[C:16](=[C:18]1\[C:19](=[O:25])[NH:20][C:21](=[O:24])[CH2:22][CH2:23]\1)/[CH3:17]>C(O)C.Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14]/[C:16](=[C:18]3\[C:19](=[O:25])[NH:20][C:21](=[O:24])[CH2:22][CH2:23]\3)/[CH3:17])=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 68698889HCID 68698889, compound

Product 1

HCID 68693656HCID 68693656, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 4-(4-methyl-1-piperazinyl)-benzenamine (43 mg, 0.23 mmol) and (3Z)-3-(1-hydroxyethylidene)-piperidine-2,6-dione (35 mg, 0.23 mmol) in absolute ethanol (1.5 mL) is added concentrated ethanolic hydrogen chloride (2 drops), which caused the precipitation of a white solid. The mixture is heated in a 65° C. oil bath for 20 minutes. Then N,N-dimethylformamide (0.4 mL) is added to the mixture and the temperature of the oil bath is increased to 70° C. An additional volume of N,N-dimethylformamide (0.6 mL) is added and the temperature of the oil bath is increased to 135° C., at which setting it stirred for 30 minutes. The mixture is stirred overnight at 130° C. After cooling to room temperature, the semi-solid reaction mixture is triturated with methanol. The solid that formed is collected by filtration and washed with diethyl ether, water, and methanol to give (3Z)-3-(1-{[4-(4-methylpiperazin-1-yl)phenyl]amino}ethylidene)piperidine-2,6-dione as a light beige solid.

Workup

  1. customthe precipitation of a white solid
  2. additionThen N,N-dimethylformamide (0.4 mL) is added to the mixture
  3. temperaturethe temperature of the oil bath is increased to 70° C
  4. additionAn additional volume of N,N-dimethylformamide (0.6 mL) is added
  5. temperaturethe temperature of the oil bath is increased to 135° C., at which
  6. stirringThe mixture is stirred overnight at 130° C
  7. temperatureAfter cooling to room temperature
  8. customthe semi-solid reaction mixture
  9. customis triturated with methanol
  10. customThe solid that formed
  11. filtrationis collected by filtration
  12. washwashed with diethyl ether, water, and methanol

Sources & evidence

ORD record
ord-df1e60b2a77c491bb3a04643561001c1
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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