Dichloromethane → 4-(1-Acetylpiperidin-4-yl)benzoic acid

HRID 1426997ノート

反応式

HRID 1426997 の反応式
ClCCl.C(Cl)(=O)C(Cl)=O.[C:10]1([CH:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:24])[CH3:23])[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:25]([O:28]CC)(=[O:27])C>O>[C:22]([N:19]1[CH2:18][CH2:17][CH:16]([C:10]2[CH:11]=[CH:12][C:13]([C:25]([OH:28])=[O:27])=[CH:14][CH:15]=2)[CH2:21][CH2:20]1)(=[O:24])[CH3:23]

参加物

6

反応物 4

HCID 6344Dichloromethane2 回HCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 11608128HCID 11608128、化合物

生成物 1

HCID 186177774-(1-Acetylpiperidin-4-yl)benzoic acid収率 61%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A mixture of aluminum chloride(III) (26 g, 195 mmol) and dichloromethane (200 mL) was stirred at 0° C., and oxalyl chloride (20 mL, 228 mmol) was dripped over 10 minutes. Then a mixture of 1-(4-phenylpiperidin-1-yl)ethanone described in Production Example 1-9 (12.3 g, 60.5 mmol) and dichloromethane (50 mL) was dripped over 30 minutes. The mixture was stirred under nitrogen atmosphere at 25° C. for 14 hours. The reaction liquid was poured onto ice and ethyl acetate (1 L) and water (1 L) were added for separation. The aqueous layer was extracted with ethyl acetate (1 L) twice, then the organic layer was washed with water (1 L) twice and then with a saturated saline solution (500 mL). The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated. Ethyl acetate was added to the concentrated residue and the product was collected by filteration and washed with ethyl acetate to obtain the title compound (9.09 g, 61%).

後処理

  1. stirringThe mixture was stirred under nitrogen atmosphere at 25° C. for 14 hours
  2. customThe reaction liquid
  3. additionwere added for separation
  4. extractionThe aqueous layer was extracted with ethyl acetate (1 L) twice
  5. washthe organic layer was washed with water (1 L) twice
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. additionEthyl acetate was added to the concentrated residue
  9. customthe product was collected by filteration
  10. washwashed with ethyl acetate

出典と根拠

ORDレコード
ord-abff31fc60c647ba903e9faad6dd93a6
出典データセット
uspto-grants-2015_01
特許番号
US08933099B2

反応ノート

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