N-[3-(4-Methylpiperazin-1-yl)propyl]-2-nitroaniline → HCID 14319495, compound

HRID 1414726Notes

Reaction equation

HRID 1414726 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][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[CH2:4][CH2:3]1>Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:6][CH2:7]1

Participants

3

Reactant 1

HCID 14319494N-[3-(4-Methylpiperazin-1-yl)propyl]-2-nitroaniline

Product 1

HCID 14319495HCID 14319495, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mechanically stirred solution of stannous chloride (1060 g., 4.71 mole) in concentrated hydrochloric acid (1200 ml.), under nitrogen, was added a solution of 2-[3-(4-methyl-1-piperazinyl)propylamino]nitrobenzene (438 g., 1.57 mole) in conc. HCl (800 ml.) at a rate sufficient to maintain the reaction temperature at 55°-60° C. The addition took place over about 1.5 hours. The heavy white precipitate which formed during the course of the addition, was stirred for an additional 1 hour. The reaction mixture was then filtered and the resultant white solid was dissolved in 3 liters of water. An equal volume of chloroform was added, the mixture was cooled to 50° C. and adjusted to pH 10, with 50% KOH. The organic layer was separated, and the cold basic aqueous phase extracted again with chloroform (1l). The organic layers were combined, dried (MgSO4) and evaporated in vacuo to give 334.8 g. of N-[3-(4-methyl-1-piperazinyl)propyl-o-phenylenediamine as a brown oil (yield 97%). A small amount of the oil was triturated with hexane. The hexane layer was cooled to 5° C. forming a tan solid which on recrystallization from benzene-hexane gave an analytical sample, m.p. 65°-67° C.

Workup

  1. temperatureto maintain the reaction temperature at 55°-60° C
  2. additionThe addition
  3. customover about 1.5 hours
  4. customThe heavy white precipitate which formed during the course of the addition
  5. filtrationThe reaction mixture was then filtered
  6. dissolutionthe resultant white solid was dissolved in 3 liters of water
  7. additionAn equal volume of chloroform was added
  8. customThe organic layer was separated
  9. extractionthe cold basic aqueous phase extracted again with chloroform (1l)
  10. dry with materialdried (MgSO4)
  11. customevaporated in vacuo
  12. customto give 334.8 g

Sources & evidence

ORD record
ord-934165b0176f4e06894f458ee8e65709
Source dataset
uspto-grants-1977_01
Patent number
US04002623

Reaction notes

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