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

HRID 637678Notes

Reaction equation

HRID 637678 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)C.[Pt]=O>[Cl:1][C:2]1[C:3]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:11]=1

Participants

4

Reactant 1

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

Product 1

HCID 202556365-Chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

200 mg of platinum oxide are added to a solution of 1.42 g (5.60 mmole) of 5-chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran in 20 ml of ethanol and the whole is hydrogenated at 3 atmospheres. The catalyst is filtered off and the filtrate is concentrated in a vacuum rotary evaporator. The residue is chromatographed over silica gel using methylene chloride as eluant. Recrystallisation from petroleum ether yields 5-chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran having a melting point of 38°-40°.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in a vacuum rotary evaporator
  3. customThe residue is chromatographed over silica gel
  4. customRecrystallisation from petroleum ether

Sources & evidence

ORD record
ord-d2448b89adee4b35aa4146dacce94c01
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

Loading…