Thiochroman → 6-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-3,4-dihydro-2H-1-benzothiopyran

HRID 327401

反応式

HRID 327401 の反応式
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.[C:11]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][C:22](Cl)=[O:23])[CH2:16][CH2:15]1)(=[O:13])[CH3:12].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[C:11]([N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][C:22]([C:9]2[CH:8]=[CH:7][C:6]3[S:1][CH2:2][CH2:3][CH2:4][C:5]=3[CH:10]=2)=[O:23])[CH2:18][CH2:19]1)(=[O:13])[CH3:12]

参加物

5

反応物 3

HCID 137415ThiochromanHCID 6451240Aluminum(III) ChlorideHCID 104659513-(1-Acetyl-4-piperidinyl)propionyl chloride

生成物 1

HCID 191084806-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-3,4-dihydro-2H-1-benzothiopyran収率 81.6%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a mixture of 3,4-dihydro-2H-1-benzothiopyran (1.5 g) and 3-(1-acetylpiperidin-4-yl)propionyl chloride (2.18 g) in 1,2-dichloroethane (20ml) was added aluminum chloride (3.2 g) portionwise at 10°-15° C. The mixture was stirred at room temperature for 2 hours then refluxed for additional 2 hours, and poured into icewater. The mixture was extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate. The solvent was distilled off. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate) to obtain 2.7 g of the title compound as a pale yellow oil.

後処理

  1. temperaturethen refluxed for additional 2 hours
  2. additionpoured into icewater
  3. extractionThe mixture was extracted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate)

出典と根拠

ORDレコード
ord-fcb979243cbd468aaea38beb0bf9cc98
出典データセット
uspto-grants-1993_12
特許番号
US05273974

関連ノート

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