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Potassium Carbonate → 7-[4-(4-benzisoxazolyl-1-piperidinyl)-butoxy]-3,4-dihydro-2(1H)-quinolinone hydrochloride

HRID 241588
ノート
印刷プレビュー

反応式

HRID 241588 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.[NH:18]1[CH2:23][CH2:22][CH:21]([C:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3S[N:25]=2)[CH2:20][CH2:19]1.C(=O)([O-])[O-:34].[K+].[K+].Cl.CCO>C(O)C.CC(C)=O>[ClH:1].[O:34]1[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:24]([CH:21]2[CH2:22][CH2:23][N:18]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]3[CH:16]=[C:15]4[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]4)=[CH:9][CH:8]=3)[CH2:19][CH2:20]2)=[N:25]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 104674677-(4-Chlorobutoxy)-1,2,3,4-tetrahydroquinolin-2-oneHCID 133240934-(3-Benzisothiazolyl) piperidineHCID 21887872Ethanol hydrochloride

生成物 1

HCID 671787567-[4-(4-benzisoxazolyl-1-piperidinyl)-butoxy]-3,4-dihydro-2(1H)-quinolinone hydrochloride収率 44%

試薬・触媒・溶媒 2

HCID 180
Acetone
溶媒
HCID 702Ethanol溶媒

実験手順

7-(4-chlorobutoxy)-3,4-dihydro-2(1H)-quinolinone (297 mg, 1 mmol), 3-(4-piperidinyl)-1,2-benzisothiazole (220 mg, 1 mmol), and anhydrous potassium carbonate powder (414 mg, 3.3 mmol) are added to 10 ml and react at reflux for 24 hours. The reaction solution is evaporated to dryness and dispersed with 20 ml of dichloromethane and 20 ml of water respectively. The organic layer is extracted with water (20 ml×2) and saturated saline (20 ml) successively, dried over anhydrous magnesium sulfate, and evaporated to dryness to obtain a light yellow powder, which is dissolved into 5 ml of acetone and stirred in an ice bath to precipitate a white solid. The white solid is filtered, washed with small amount of acetone, and dried to obtain 260 mg of a whiter powder. The whiter powder is dissolved into anhydrous ethanol and thereto is drop-added HCl/EtOH to adjust to pH=2 to precipitate a white deposit, which is filtered out and recrystallized in anhydrous ethanol to obtain 200 mg of a product, with a yield of 44%.

後処理

  1. customreact
  2. temperatureat reflux for 24 hours
  3. customThe reaction solution is evaporated to dryness
  4. additiondispersed with 20 ml of dichloromethane and 20 ml of water respectively
  5. extractionThe organic layer is extracted with water (20 ml×2) and saturated saline (20 ml) successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customto obtain a light yellow powder, which
  9. customto precipitate a white solid
  10. filtrationThe white solid is filtered
  11. washwashed with small amount of acetone
  12. customdried
  13. customto obtain 260 mg of a whiter powder
  14. customto precipitate a white deposit, which
  15. filtrationis filtered out
  16. customrecrystallized in anhydrous ethanol

出典と根拠

ORDレコード
ord-db1f90e93f864f7693a5cfd999412ff1
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653069B2

反応ノート

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