1-Methylpiperazine → (2-Methoxy-3-nitro-phenyl)-(4-methyl-piperazin-1-yl)-methanone

HRID 1262309Notes

Reaction equation

HRID 1262309 reaction equation
[CH3:1][O:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O.ON1C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([N:19]1[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]1)=[O:7]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 120151952-Methoxy-3-nitrobenzoic acid

Product 1

HCID 66712414(2-Methoxy-3-nitro-phenyl)-(4-methyl-piperazin-1-yl)-methanoneYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methoxy-3-nitro-benzoic acid (1.20 g, 6.09 mmol), 1-Methylpiperazine (1.01 mL, 9.13 mmol) N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1750 mg, 9.13 mmol, 1-hydroxybenzotriazole hydrate (1.45 g, 9.13 mmole) and N,N-Dimethylformamide (40.4 mL) were combined into a vial and stirred at room temperature for 1 hour. LCMS showed complete conversion to product. Diluted reaction mixture with saturated NaHCO3 and filtered off resulting ppt. The solid was filtered and washed with water. The solid was dried under vacuum overnight to give (2-Methoxy-3-nitro-phenyl)-(4-methyl-piperazin-1-yl)-methanone as a white solid (0.70 g, 44%)

Workup

  1. additionDiluted
  2. filtrationfiltered off
  3. customresulting ppt
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-c0a62e1f49304c1ea7042b99df886f66
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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