Potassium Carbonate → Methyl 4-(4-methylpiperazin-1-yl)-3-nitrobenzoate

HRID 1472203Notes

Reaction equation

HRID 1472203 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 2904229Methyl 4-(4-methylpiperazin-1-yl)-3-nitrobenzoateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoro-3-nitro-benzoic acid methyl ester (10 g, 50.2 mmol), K2CO3 (7 g, 50.2 mmol) and 1-methyl-piperazine (11.2 mL, 100.4 mmol, 2 eq.) in 200 mL of N,N-dimethylformamide was stirred at 100° C. for 1 h. The solvent was then evaporated, the residue taken-up with water, extracted with ethyl acetate, dried over sodium sulphate and evaporated to dryness. The crude was purified by flash chromatography on silica gel, using a mixture dichloromethane-MeOH 9:1 as eluant, affording 14 g of the title compound as orange oil.

Workup

  1. customThe solvent was then evaporated
  2. extractionthe residue taken-up with water, extracted with ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness
  5. customThe crude was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-cc32aa258af042b9ad6dbfa8a1833654
Source dataset
uspto-grants-2015_04
Patent number
US09012487B2

Reaction notes

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