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

HRID 1190868Notes

Reaction equation

HRID 1190868 reaction equation
Cl[Sn]Cl.Cl.[C:5]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)([CH3:8])([CH3:7])[CH3:6].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:5]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)[NH2:17])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 67247988Tert-butyl({[2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methyl})amine

Product 1

HCID 672478243-[(Tert-butylamino)methyl]-4-(4-methylpiperazin-1-yl)anilineYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of SnCl2 (0.364 g, 4 eq), 1.44 mL of HCl 1M and 5 mL of THF was added to a solution of tert-butyl({[2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methyl})amine (0.147 g, 0.48 mmol) in 20 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//85/15/1) to yield expected compound as a brown oil (65 mg, 49% 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//85/15/1)

Sources & evidence

ORD record
ord-fa47b8900ed54bf59f7c1b252ef1d3ce
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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