Sodium Hydroxide → HCID 13139730, compound

HRID 1788672Notes

Reaction equation

HRID 1788672 reaction equation
[Cl-:1].[Cl-].[C:3]1([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]([C:20]3[CH:28]=[CH:27][C:23]4[O:24][CH2:25][O:26][C:22]=4[CH:21]=3)=[O:19])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[BH4-].[Na+]>CO>[ClH:1].[ClH:1].[C:3]1([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH:18]([C:20]3[CH:28]=[CH:27][C:23]4[O:24][CH2:25][O:26][C:22]=4[CH:21]=3)[OH:19])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86741691HCID 86741691, compound

Product 1

HCID 13139730HCID 13139730, compoundYield 182.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-[4-(4-Phenyl-1-piperazinyl)butyryl]-1,3-benzodioxole dichloride (3.8 g) as prepared in Example 2 was suspended in methanol (50 ml) and 2N sodium hydroxide solution (4.5 ml) and then sodium borohydride (0.5 g) were added. The mixture was stirred for 10 hours at room temperature and the solvent was then distilled off. The residue was extracted with ethyl acetate and the extract was washed with saturated saline and dried over anhydrous sodium sulfate. Thereafter, 20% hydrogen chloride in ethanol (4.9 ml) was added and the resulting crystals were collected by filtration and recrystallized from ethanol to give 5-[4-(4-phenyl-1-piperazinyl)-1-hydroxybutyl]-1,3-benzodioxole dihydrochloride (3.5 g, 62% yield). The characteristics of this compound are shown in Table 3 as Compound 19.

Workup

  1. distillationthe solvent was then distilled off
  2. extractionThe residue was extracted with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. additionThereafter, 20% hydrogen chloride in ethanol (4.9 ml) was added
  6. filtrationthe resulting crystals were collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7f5d715623e841f083ce610c50112df4
Source dataset
uspto-grants-1987_08
Patent number
US04684651

Reaction notes

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