1-Methylpyrrolidine → N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzene

HRID 1391393Notes

Reaction equation

HRID 1391393 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CN1CCCC1.[NH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:27][N:24]1[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][CH2:18][NH:17][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 84541-MethylpyrrolidineHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 783281-(3-Aminopropyl)-4-methylpiperazine

Product 1

HCID 21975010N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzeneYield 81.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2 g of 4-fluoronitrobenzene were added to a solution of 20 ml of N-methyl-pyrrolidine, 2.67 g of N-(3-aminopropyl)-N′-methylpiperazine and 2.35 g of K2CO3. The reaction medium was heated at 60° C. for 10 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 3.22 g of N-[3-(4-methyl-piperazin-1-yl)propyl]-4-nitro-1-aminobenzene (9) were obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. customThe yellow precipitate formed
  3. filtrationwas filtered off
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-759f972a92ab4b6e88f73095ee87a70f
Source dataset
uspto-grants-2008_03
Patent number
US07338536B2

Reaction notes

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