Stannous chloride dihydrate → 4-(4-Methylpiperazin-1-yl)aniline

HRID 1357479Notes

Reaction equation

HRID 1357479 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.O.O.[Sn](Cl)Cl>CN(C)C=O>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 28251981-Methyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 7372534-(4-Methylpiperazin-1-yl)anilineYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.999 g (4.5 mmol) of 1-methyl-4-(4-nitrophenyl)piperazine, 10.15 g (45 mmol) of tin(II)chloride dihydrate and 20 ml of dimethylformamide were mixed and stirred overnight at 80° C. Most of dimethylformamide was evaporated under vacuum. The remaining slurry was poured into ice water, neutralized with a sodium bicarbonate (sat.) solution, and filtered. The filtrate was extracted several times with ethylacetate and chloroform to provide 0.636 g (74%) of 4-(4-methylpiperazin-1-yl)aniline.

Workup

  1. customMost of dimethylformamide was evaporated under vacuum
  2. additionThe remaining slurry was poured into ice water
  3. filtrationfiltered
  4. extractionThe filtrate was extracted several times with ethylacetate and chloroform

Sources & evidence

ORD record
ord-10ca94b94c2844938dffa13c91211877
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

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