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Hydrochloric Acid → 4-(4-Methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl)methyl]aniline

HRID 1190865
Notes
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Reaction equation

HRID 1190865 reaction equation
Cl[Sn]Cl.Cl.[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)[CH2:8][CH2:7]1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[CH2:21][N:22]2[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]2)[CH2:10][CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 672468861-Methyl-4-{2-[(4-methylpiperazin-1-yl)methyl]-4-nitrophenyl}piperazine

Product 1

HCID 672492344-(4-Methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl)methyl]anilineYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of SnCl2 (0.398 g, 2.1 mmol), 1.6 mL of HCl 1M and 5 mL of THF was added to a solution of 1-methyl-4-{2-[(4-methylpiperazin-1-yl)methyl]-4-nitrophenyl}piperazine (0.175 g, 2.5 eq) in 15 mL of THF. The reaction mixture was refluxed for 3 h and allowed to cool to room temperature. A saturated aqueous solution of Na2CO3 was added. The aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (DCM/MeOH/NH4OH//8/2/0.1) to yield expected compound as a brown oil (100 mg, 63% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (DCM/MeOH/NH4OH//8/2/0.1)

Sources & evidence

ORD record
ord-6040fbecdcbf43869eac1b2d1a3fe700
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680095B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes