2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Chloro-6-(piperidin-1-yl)-benzofuran

HRID 637677Notes

Reaction equation

HRID 637677 reaction equation
[Cl:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 202556365-Chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.37 g (10.0 mmole) of 5-chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran and 2.27 g (10.0 mmole) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in 200 ml of dioxane is boiled under reflux for 12 hours. The reaction mixture is cooled and filtered and the filtrate is 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. temperatureunder reflux for 12 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated in a vacuum rotary evaporator
  5. customThe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-d6d5f43e4b9a41688ac506ea332bdce3
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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