Sulfuric Acid → HCID 18423178, compound

HRID 1282085Notes

Reaction equation

HRID 1282085 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2N)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:19].N([O-])=O.[Na+].[OH-].[Na+].C(Cl)(=O)C>O.CO.C(Cl)(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[OH:19])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 184231291-[4-(2-Amino-4-fluorophenyl)piperazin-1-yl]ethan-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 18423178HCID 18423178, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of 1-acetyl-4-(2-amino-4-fluorophenyl)piperazine (25 g) and conc. sulfuric acid (42 ml) in water (210 ml) was added dropwise a solution of sodium nitrite (13 g) in water (46 ml) under ice-cooling. This reaction mixture was stirred at the same temperature for 4 hr and at room temperature for 6 hr. To the reaction mixture was added an aqueous sodium hydroxide solution to make it alkaline and acetyl chloride was added dropwise. The mixture was stirred at the same temperature for 30 min, passed through Celite and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a black oil. The oil was subjected to silica gel column chromatography (developing solvent; chloroform:methanol=9:1) to give a black solid. This solid was recrystallized from ethyl acetate-isopropyl ether to give the title compound (0.66 g) as a pale-brown solid, m.p.=183-185° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give a black oil
  8. customto give a black solid
  9. customThis solid was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-b56da507147a4edaa12539e96d476ef7
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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