Sulfuric Acid → HCID 19841128, compound

HRID 1638676Notes

Reaction equation

HRID 1638676 reaction equation
[F:1][C:2]1[C:3]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[C:4]([C:7]([F:13])=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH2:5][OH:6].S(=O)(=O)(O)O.[C:32](=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CO>[F:13][C:7]1[C:4]([CH2:5][O:6][CH3:32])=[C:3]([N:14]2[CH2:15][CH2:16][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][CH2:19]2)[C:2]([F:1])=[CH:9][C:8]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 54066861HCID 54066861, compound

Product 1

HCID 19841128HCID 19841128, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,6-difluoro-2-(4-benzyl-1-piperazinyl)-5-nitrobenzyl alcohol (15.4 g) in methanol (400 ml) is added gradually conc. sulfuric acid (80 ml) with stirring under ice cooling. After the addition, the mixture is refluxed for 30 hours, and thereto is further added conc. sulfuric acid (10 ml), and the mixture is further refluxed for 20 hours. After cooling to room temperature, the reaction mixture is adjusted to below pH 8 with aqueous saturated potassium carbonate and aqueous saturated sodium hydrogen carbonate and then extracted with ethyl acetate. The extract is dried over magnesium sulfate, and then the solvent is distilled off. The residue is purified by silica gel column chromatography (solvent, dichloromethane) to give 2,5-difluoro-4-(4-benzyl-1-piperazinyl)-3-methoxymethylnitrobenzene (12.9 g).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is refluxed for 30 hours
  3. temperaturethe mixture is further refluxed for 20 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract is dried over magnesium sulfate
  6. distillationthe solvent is distilled off
  7. customThe residue is purified by silica gel column chromatography (solvent, dichloromethane)

Sources & evidence

ORD record
ord-c3978c224f2b4f64b9478d260b999008
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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