Sodium Iodide → 1-[4-(3-Piperidin-1-ylpropoxy)phenyl]ethanone

HRID 221852

反応式

HRID 221852 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Cl.Cl[CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[NH3:16].[N:16]1([CH2:15][CH2:14][CH2:13][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochloride

生成物 2

HCID 222AmmoniaHCID 22001121-[4-(3-Piperidin-1-ylpropoxy)phenyl]ethanone収率 6.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 5.97 g of 4′-hydroxyacetophenone (43.8 mmol), 13.0 g of 1-(3-chloropropyl)-piperidine hydrochloride (65.8 mmol), 12.70 g of potassium carbonate (91.89 mmol), and 3.28 g of sodium iodide (21.9 mmol) in 100 mL dry acetone was stirred at reflux. After 1.5 h, the reaction was cooled to room temperature, filtered and concentrated. Ethyl acetate was added and the white solid that remained was filtered off. The filtrate was concentrated in vacuo and the crude residue was purified via silica gel chromatography using a gradient of ethyl acetate then 400:20:10 ethyl acetate: 7N ammonia in methanol:methanol to yield 583 mg of 1-[4-(3-piperidin-1-ylpropoxy)phenyl]ethanone as an oil. MS m/z 265 (M+H).

後処理

  1. temperatureat reflux
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionEthyl acetate was added
  5. filtrationthe white solid that remained was filtered off
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe crude residue was purified via silica gel chromatography

出典と根拠

ORDレコード
ord-b682f420bbec46bfa892f79c2171f154
出典データセット
uspto-grants-2012_06
特許番号
US08207168B2

関連ノート

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