Hydrochloric Acid → 1-(4-Chlorobenzyl)-4-(2,4-dichlorocinnamyl)piperazine dihydrochloride

HRID 1252090Notes

Reaction equation

HRID 1252090 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13](=O)[CH:14]=[CH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[ClH:34]>O1CCCC1>[ClH:1].[ClH:34].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH:14]=[CH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[CH2:9][CH2:8]2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 536729351-(4-Chlorobenzyl)-4-(2,4-dichlorocinnamoyl)piperazine

Product 1

HCID 30653721-(4-Chlorobenzyl)-4-(2,4-dichlorocinnamyl)piperazine dihydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Chlorobenzyl)-4-(2,4-dichlorocinnamoyl)piperazine (1.0 g, 2.44 mmole) (the compound prepared in Reference Example 1) is dissolved in anhydrous tetrahydrofuran (10 ml), and thereto is added in portions lithium aluminum hydride (0.1 g, 2.63 mmole) at room temperature. After the addition, the mixture is stirred at room temperature for one hour. After adding water in portions, the reaction mixture is neutralized to approximately neutral with 3N hydrochloric acid, and then is extracted with ethyl acetate. The ethyl acetate layer is separated, washed with water, dried over anhydrous magnesium sulfate, and then the solvent is distilled off. The resulting oily substance is dissolved in ethanol (5 ml), and thereto is added an ethanol solution (10 ml) of conc. hydrochloric acid (0.5 ml), and the precipitated crystals are separated by filtration. The product is recrystallized from water-ethanol to give the title compound (0.2 g). The product has the same physical properties as those of the compound prepared in Example 1-(1).

Workup

  1. additionAfter the addition
  2. extractionis extracted with ethyl acetate
  3. customThe ethyl acetate layer is separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off
  7. dissolutionThe resulting oily substance is dissolved in ethanol (5 ml)
  8. additionis added an ethanol solution (10 ml) of conc. hydrochloric acid (0.5 ml)
  9. customthe precipitated crystals are separated by filtration
  10. customThe product is recrystallized from water-ethanol

Sources & evidence

ORD record
ord-77385086c608458c951b8d46ea1aa407
Source dataset
uspto-grants-1988_05
Patent number
US04742062

Reaction notes

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