Potassium Carbonate → 4-amino-5-chloro-N-(1-(6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexyl)-piperidin-4-ylmethyl)-2-methoxybenzamide

HRID 344382

反応式

HRID 344382 の反応式
Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+].BrCCCCCC[C:35]1[CH:45]=[CH:44][CH:43]=[C:37]2[C:38]([NH:40][C:41](=[O:42])[C:36]=12)=O>CN(C)C=O>[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:5][CH2:4][CH2:3][CH2:18][CH2:17][CH2:38][N:40]3[C:41](=[O:42])[C:36]4[C:35](=[CH:45][CH:44]=[CH:43][CH:37]=4)[C:22]3=[O:25])[CH2:15][CH2:16]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 219308536-BromohexylphthalimideHCID 667809414-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride

生成物 1

HCID 545206764-amino-5-chloro-N-(1-(6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexyl)-piperidin-4-ylmethyl)-2-methoxybenzamide収率 62.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride (8.5 g) was dissolved in dimethylformamide (100 ml). Potassium carbonate (10.5 g) and 6-bromohexylphthalimide (7.2 g) were added, and the mixture was stirred at 70° C. for 16 hr. The reaction mixture was concentrated under reduced pressure and the residue was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 4.2 g of 4-amino-5-chloro-N-(1-(6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexyl)-piperidin-4-ylmethyl)-2-methoxybenzamide.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-b0302d1f48d04f79a5fc161d508661df
出典データセット
uspto-grants-1999_01
特許番号
US05864039

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