Methanol → 1-[4-(3,4-Diamino-5-methyl-phenyl)-piperazin-1-yl]-ethanone

HRID 970348Notes

Reaction equation

HRID 970348 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[CH2:13][CH2:12]2)=[CH:4][C:3]=1[CH3:20].CO.[H][H]>[Pd].C(O)(=O)C>[NH2:8][C:7]1[CH:6]=[C:5]([N:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16]2)[CH:4]=[C:3]([CH3:20])[C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 220210541-[4-(4-Amino-3-methyl-5-nitro-phenyl)-piperazin-1-yl]-ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 220210411-[4-(3,4-Diamino-5-methyl-phenyl)-piperazin-1-yl]-ethanoneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To 1-[4-(4-amino-3-methyl-5-nitro-phenyl)-piperazin-1-yl]-ethanone (4.5 g, 16.2 mmol) and 10% palladium on carbon (400 mg) were added methanol (50 mL) and acetic acid (5 mL) under nitrogen. The reaction mixture was stirred under hydrogen atmosphere (hydrogen balloon) for 14 h. The dark solution was filtered through a pad of celite and the filtercake was washed with methanol. Concentration of the filtrate gave the title compound (4.00 g, 100%) which was used for the next step without purification. LCMS (M+H)+ m/z 207 (t=0.41 min.). Procedure for the Preparation of 5-fluoro-3-methyl-2-nitro-aniline:

Workup

  1. filtrationThe dark solution was filtered through a pad of celite
  2. washthe filtercake was washed with methanol

Sources & evidence

ORD record
ord-91ef9a6269d04436a7d88841edc4dddb
Source dataset
uspto-grants-2007_12
Patent number
US07312215B2

Reaction notes

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