HCID 764809, compound → HCID 13544863, compound

HRID 1390973Notes

Reaction equation

HRID 1390973 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CCOCC.O.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:13][CH2:12]2)=[CH:16][CH:17]=1

Participants

5

Reactant 1

HCID 764809HCID 764809, compound

Product 1

HCID 13544863HCID 13544863, compoundYield 66.3%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 1-(4-fluorophenyl)-4-[ (4-nitrophenyl)methyl ]piperazine (1.5 g, 0.005 M) in 15 ml of anhydrous ether is added dropwise a solution of 15 ml of titanium trichloride in water (20% solution in water), under nitrogen at room temperature. After complete addition, the mixture is quenched with 10% ammonium hydroxide solution and extracted with methylene chloride. The methylene chloride solution is washed with water, dried (anhydrous sodium sulfate), and concentrated to a yellow solid. This, after recrystallization from ethyl acetate/Skellysolve® B, gives 900 mg (64%) of white crystalline 1-[ (4-aminophenyl)methyl ]-4-(4-fluorophenyl)piperazine of melting point 130° - 132° C.

Workup

  1. customat room temperature
  2. additionAfter complete addition
  3. customthe mixture is quenched with 10% ammonium hydroxide solution
  4. extractionextracted with methylene chloride
  5. washThe methylene chloride solution is washed with water
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated to a yellow solid
  8. customThis, after recrystallization from ethyl acetate/Skellysolve® B

Sources & evidence

ORD record
ord-3b834d0dba7c445a9f61cf71ae4dfa70
Source dataset
uspto-grants-1979_02
Patent number
US04140775

Reaction notes

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