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

HRID 637684Notes

Reaction equation

HRID 637684 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][CH:8](O)[CH2:7][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 202556345-Chloro-2-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

5 mg of platinum oxide are added to a solution of 250 mg (1.00 mmole) of crude 5-chloro-2-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran in 5 ml of absolute ethanol and the whole is hydrogenated at room temperature and 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. customis hydrogenated at room temperature
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated in a vacuum rotary evaporator
  4. customThe residue is chromatographed over silica gel
  5. customRecrystallisation from petroleum ether

Sources & evidence

ORD record
ord-1c1b54bbe5ea42f68d170fbcc0f906ad
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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