Sodium Carbonate → 5-Chloro-6-(piperidin-1-yl)-benzofuran

HRID 637674Notes

Reaction equation

HRID 637674 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][C:5]2[O:9][CH2:8][CH:7](O)[C:6]=2[CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 202556505-Chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

Product 1

HCID 202556395-Chloro-6-(piperidin-1-yl)-benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.40 g (9.4 mmole) of 5-chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran in 25 g of polyphosphoric acid is maintained at 60° for 20 minutes, then ice and water are added and the whole is adjusted to pH 7 with solid sodium carbonate. The reaction mixture is extracted twice with methylene chloride. The organic phases are washed with water, combined, dried over magnesium sulphate and concentrated in a vacuum rotary evaporator. The residue is chromatographed over silica gel using methylene chloride as eluant (Rf =0.63). In that manner, 5-chloro-6-(piperidin-1-yl)-benzofuran is obtained in the form of an oil which distills at 96°-97°/1.5 torr.

Workup

  1. extractionThe reaction mixture is extracted twice with methylene chloride
  2. washThe organic phases are washed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in a vacuum rotary evaporator
  5. customThe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-8eb28eb5fc404e3ab5df7add0fd2fd64
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

Loading…