Hydrazine hydrate (1:1) → N~1~-[3-(4-Methylpiperazin-1-yl)propyl]benzene-1,4-diamine

HRID 640983

Reaction equation

HRID 640983 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.O.NN>[Ni].CCO>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21975010N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzene

Product 1

HCID 21975027N~1~-[3-(4-Methylpiperazin-1-yl)propyl]benzene-1,4-diamineYield 83.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A 50 mL round bottom flask was charged with [3-(4-Methyl-piperazin-1-yl)-propyl]-(4-nitro-phenyl)-amine (as prepared in step 1 above; 0.365 g, 1.31 mmol) and EtOH (5 mL). Hydrazine Hydrate (0.286 mL, 9.17 mmol) was then added to the solution. Excess RaNi was then added in dropwise until gas evolution from the solution ceased. The suspension was then allowed to stir for an additional 45 minutes at 65° C. The suspension was cooled to room temperature and then filtered over celite. The celite was washed with MeOH (˜20 mL) and the combined organic solutions were then concentrated in vacuo affording pure N-[3-(4-Methyl-piperazin-1-yl)-propyl]-benzene-1,4-diamine as a light brown oil (0.269 g, 1.09 mmol, 83% yield).

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationfiltered over celite
  3. washThe celite was washed with MeOH (˜20 mL)
  4. concentrationthe combined organic solutions were then concentrated in vacuo

Sources & evidence

ORD record
ord-f4db72c518da41a68aadc7968f1f62c7
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Linked notes

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