1-(p-Fluoro-phenyl)-4-[4-(2-oxo-1-benzimidazolinyl)-1,2,3,6-tetrahydro-1-pyridyl]-1-butanol → Droperidol

HRID 1578393Notes

Reaction equation

HRID 1578393 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:28])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH:16]=[C:15]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[O:27])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[O:27]=[C:19]1[N:18]([C:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:28])[CH2:13][CH:14]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20]1

Participants

4

Reactant 1

HCID 215599841-(p-Fluoro-phenyl)-4-[4-(2-oxo-1-benzimidazolinyl)-1,2,3,6-tetrahydro-1-pyridyl]-1-butanol

Product 1

HCID 3168Droperidol

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2.0 g of 1-(p-fluoro-phenyl)-4-[4-(2-oxo-1-benzimidazolinyl)-1,2,3,6-tetrahydro-1-pyridyl]-1-butanol in 60 ml of chloroform at room temperature, was added portionwise 3.2 g of a fine powder of manganese dioxide. After completion of addition, the mixture was stirred for another 2 hours at room temperature, and the precipitate was filtered off. The filtrate was concentrated to dryness under reduced pressure, and the residue was recrystallized from dioxane containing water, to obtain γ-[4-(2-oxo-1-benzimidazolinyl)-1,2,3,6-tetrahydro-1-pyridyl]-p-fluorobutyrophenone, melting at 146° - 147 5°C.

Workup

  1. additionAfter completion of addition
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. customthe residue was recrystallized from dioxane
  5. additioncontaining water

Sources & evidence

ORD record
ord-3bbf78a810714b19b60b7b5a6d10cd9a
Source dataset
uspto-grants-1976_02
Patent number
US03936468

Reaction notes

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