2-Piperidone → HCID 21593249, compound

HRID 1609458Notes

Reaction equation

HRID 1609458 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Cl>CN(C)C=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]

Participants

5

Reactant 3

HCID 126652-PiperidoneHCID 24758Sodium hydrideHCID 699943-Methoxybenzyl chloride

Product 1

HCID 21593249HCID 21593249, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
65 °C

Procedure

In 6 ml of N,N-dimethylformamide was suspended 0.8 g of 60% sodium hydride and thereto was added dropwise a solution of 1.98 g of 2-piperidone in 8 ml of N,N-dimethylformamide under a stream of argon and with ice cooling. Then, to the mixture was added dropwise a solution of 2.82 g of 3-methoxybenzyl chloride in 8 ml of N,N-dimethylformamide at room temperature. The mixture was stirred at 65° C. for 8 hours. After cooling, to the reaction mixture were added ice-cold water and the mixture was extracted with diethyl ether. The extract was purified by a silica gel column chromatography (chloroform:methanol=20:1) to give 4.3 g of 1-(3-methoxybenzyl)-2-piperidone. This compound was heated in 10 ml of 47% hydrobromic acid for 12 hours. The mixture was made alkaline with addition of sodium carbonate and extracted with chloroform. After removing the solvent at a reduced pressure, 2.3 g (yield 57%) of 1-(3-hydroxybenzyl)-2-piperidone was obtained.

Workup

  1. temperatureAfter cooling, to the reaction mixture
  2. additionwere added ice-cold water
  3. extractionthe mixture was extracted with diethyl ether
  4. customThe extract was purified by a silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-af6ff230b5144918b6bccb9d0d248745
Source dataset
uspto-grants-1995_03
Patent number
US05401739

Reaction notes

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