Water → (3-Methoxy-4-nitrophenyl)(4-methylpiperazin-1-yl)methanone

HRID 1503851Notes

Reaction equation

HRID 1503851 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([OH:8])=O.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O>S(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([N:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)=[O:8])[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 787643-Methoxy-4-nitrobenzoic acid

Product 1

HCID 66711301(3-Methoxy-4-nitrophenyl)(4-methylpiperazin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-methoxy-4-nitrobenzoic acid (6.81 g, 34.54 mmol) in sulfurous dichloride (50 mL) was stirred at reflux for 8 hours. After cooling to ambient temperature, the mixture was concentrated under vacuum and the residue was dissolved in dichloromethane (60 mL). 1-Methylpiperazine (3.6 g, 36.27 mmol) was added at 0° C. and the mixture was stirred at ambient temperature for 4 hours. The mixture was poured into water (100 mL) and extracted with dichloromethane (2×200 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to provide the crude title compound. MS: 280.2 (M+H+).

Workup

  1. temperatureat reflux for 8 hours
  2. concentrationthe mixture was concentrated under vacuum
  3. dissolutionthe residue was dissolved in dichloromethane (60 mL)
  4. extractionextracted with dichloromethane (2×200 mL)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5bb7849ade494e3b803a252a0398dfb2
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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