5-chloro-6-(piperidin-1-yl)-benzofuran-3(2H)-one → 5-Chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

HRID 637676Notes

Reaction equation

HRID 637676 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][C: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 202556645-chloro-6-(piperidin-1-yl)-benzofuran-3(2H)-one

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 1.38 g (5.5 mmole) of 5-chloro-6-(piperidin-1-yl)-benzofuran-3(2H)-one 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-1acbea09b980480ca2d8d59231e3c4db
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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