2-Piperidone → 1-(4-Methoxybenzyl)piperidin-2-one

HRID 1810776ノート

反応式

HRID 1810776 の反応式
[OH-].[K+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]2=[O:9])=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 126652-PiperidoneHCID 14797Potassium HydroxideHCID 699934-Methyloxybenzyl chloride

生成物 1

HCID 115068011-(4-Methoxybenzyl)piperidin-2-one収率 52.1%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒2 回

実験手順

A suspension of potassium hydroxide (85%, 18.6 g) and tetrabutylammonium bromide (4.88 g) in toluene (250 ml) was refluxed overnight under nitrogen atmosphere using Deenschtark device. The mixture was cooled to 80° C., to which a solution of 2-piperidone (25.0 g) and 4-methoxybenzylchloride (51.3 g) in toluene (50 ml) were added dropwise. After refluxing for 8 hours, the reaction mixture was returned to room temperature and washed with water and saturated brine. The resultant was dried with magnesium sulfate, after which the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give 1-(4-methoxybenzyl)piperidin-2-one (28.8 g) as a colorless oily material.

後処理

  1. temperaturewas refluxed overnight under nitrogen atmosphere
  2. additionwere added dropwise
  3. temperatureAfter refluxing for 8 hours
  4. customwas returned to room temperature
  5. washwashed with water and saturated brine
  6. dry with materialThe resultant was dried with magnesium sulfate
  7. distillationafter which the solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-79bcaf0de24f418abf078a5825988026
出典データセット
uspto-grants-2013_01
特許番号
US08362058B2

反応ノート

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