Water → HCID 68634606, compound

HRID 2244043Notes

Reaction equation

HRID 2244043 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=2[N+:25]([O-:27])=[O:26])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 68634606HCID 68634606, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Piperazine-1-carboxylic acid benzyl ester (8.00 g; 36.3 mmol), 2-fluoro-4-methyl-1-nitro-benzene (4.70 g; 30.3 mmol) and potassium carbonate (8.5 g; 61.5 mmol) were stirred 3 hours in 50 mL DMSO at 80° C. The reaction mixture was cooled to room temperature and 250 mL Water was added. The mixture was extracted with diethyl ether (2×250 mL). The organic phase was washed with water (100 mL), 1 N HCl (2×100 mL), brine (2×100 mL), dried with MgSO4 and concentrated in vacuo to give 10.5 g (29.5 mmol; 97.6%) 4-(5-methyl-2-nitro-phenyl)-piperazine-1-carboxylic acid benzyl ester.

Workup

  1. extractionThe mixture was extracted with diethyl ether (2×250 mL)
  2. washThe organic phase was washed with water (100 mL), 1 N HCl (2×100 mL), brine (2×100 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-280a3174737343e9ab0eff794c1365c2
Source dataset
uspto-grants-2010_03
Patent number
US07678800B2

Reaction notes

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