5-Chloro-3-hydroxy-3-methyl-6-(piperidin-1-yl)-2,3-dihydrobenzofuran → 5-Chloro-3-methyl-6-(piperidin-1-yl)-benzofuran

HRID 637672Notes

Reaction equation

HRID 637672 reaction equation
[Cl:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][C:5]2[O:9][CH2:8][C:7](O)([CH3:10])[C:6]=2[CH:12]=1>C(O)(=O)C>[Cl:1][C:2]1[C:3]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:12]=1

Participants

3

Reactant 1

HCID 202556555-Chloro-3-hydroxy-3-methyl-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

Product 1

HCID 202556485-Chloro-3-methyl-6-(piperidin-1-yl)-benzofuran

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.4 g (5.2 mmole) of 5-chloro-3-hydroxy-3-methyl-6-(piperidin-1-yl)-2,3-dihydrobenzofuran in 20 ml of acetic acid/5N hydrochloric acid 1:1 is maintained at 85° for one hour. The reaction mixture is concentrated in a vacuum rotary evaporator, water is added to the residue and the whole is adjusted to pH 7 with saturated sodium carbonate solution and extracted 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 chloroform as eluant yields 5-chloro-3-methyl-6-(piperidin-1-yl)-benzofuran which, after recrystallisation from petroleum ether, melts at 82°-84°.

Workup

  1. concentrationThe reaction mixture is concentrated in a vacuum rotary evaporator, water
  2. additionis added to the residue
  3. extractionextracted with methylene chloride
  4. washThe organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in a vacuum rotary evaporator

Sources & evidence

ORD record
ord-89f54145c9bd478fa1cad1eda469aae3
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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