Ammonium Chloride → 5-Chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

HRID 637675Notes

Reaction equation

HRID 637675 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:6][C:7]2[O:11][CH2:10][C:9](=[O:12])[C:8]=2[CH:13]=1.[Cl-].[NH4+]>CO.O>[Cl:3][C:4]1[C:5]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:6][C:7]2[O:11][CH2:10][CH:9]([OH:12])[C:8]=2[CH:13]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 202556645-chloro-6-(piperidin-1-yl)-benzofuran-3(2H)-one

Product 1

HCID 202556505-Chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

528 mg (13.1 mmole) of sodium borohydride are added to a solution, cooled to 0°, of 3.3 g (13.1 mmole) of 5-chloro-6-(piperidin-1-yl)-benzofuran-3(2H)-one, according to Example 2, in 80 ml of methanol. The whole is subsequently stirred for a further 4 hours at 0°. The reaction mixture is diluted with water, adjusted to pH 6-7 with dilute ammonium chloride solution and extracted several times with methylene chloride. The organic phases are washed with water, combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. Chromatography over silica gel using methylene chloride as eluant (Rf =0.12) yields 5-chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran in the form of an oil.

Workup

  1. extractionextracted several times with methylene chloride
  2. washThe organic phases are washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in a vacuum rotary evaporator

Sources & evidence

ORD record
ord-c10dc786ee5a4d8982f544c90c5d57c1
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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