Sodium Hydroxide → HCID 21563338, compound

HRID 1580629Notes

Reaction equation

HRID 1580629 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH:13]([F:25])[CH2:14][CH:15](N)[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N([O-])=O.[Na+].[PH2](O)=O.[OH-].[Na+]>Cl.O>[C:1]1([N:7]2[CH2:8][CH2:9][N:10]([CH:13]([F:25])[CH2:14][CH2:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 21563376HCID 21563376, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21563338HCID 21563338, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a cooled solution of 3.4 g of γ-(4-phenylpiperazino)-2-amino-4-fluorobutyrophenone in 100 ml of lN hydrochloric acid was added dropwise 0.7 g of sodium nitrite dissolved in 10 ml of water under stirring at a temperature below 0°C. The resulting diazonium salt solution was added to a cooled solution of 20 ml of 50 % hypophosphorous acid with vigorous stirring. The stirring was continued for 90 minutes below 0°C and the reaction mixture was stored in a refrigerator overnight. The cold reaction mixture was made alkaline with 10 % sodium hydroxide and extracted with ether. The etheral layer was washed with water, dried over anhydrous sodium sulfate and concentrated to an oily residue, which was crystallized on standing. Recrystallization from isopropanol gave γ-(4-phenylpiperazino)-4-fluorobutyrophenone, melting point 104.0°-106.0°C.

Workup

  1. customwas stored in a refrigerator overnight
  2. customThe cold reaction mixture
  3. extractionextracted with ether
  4. washThe etheral layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to an oily residue, which
  7. customwas crystallized
  8. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-045a26d94d6241df8cb0b62817426031
Source dataset
uspto-grants-1976_01
Patent number
US03933824

Reaction notes

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