反応 #5683

反応方程式

dicyclohexylcarbodiimide

dimethylaminopyridine

dimethylaminopyridine hydrochloride

5-hydroxymethyl-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

sodium hydrogen carbonate

N,N-dimethylglycine hydrochloride

→

5-[(2-dimethylaminoacetyloxy)methyl]-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine hydrochloride

収率 141.6%

溶媒

acetic acid

methanol

chloroform

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture is stirred at room temperature overnight
2. 2
   workup.STIRRINGthe mixture is stirred at room temperature for two hours
3. 3
   抽出the mixture is extracted with dichloromethane
4. 4
   乾燥the extract is dried over magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent is distilled off under reduced pressure
6. 6
   その他the resulting residue is purified by silica gel column chromatography (eluent; methyl acetate)
7. 7
   workup.ADDITIONis added
8. 8
   workup.ADDITIONa mixture of hydrochloric acid/methanol
9. 9
   workup.STIRRINGThe mixture is stirred at room temperature for one hour

実験手順

In a solution of 5-hydroxymethyl-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g) in chloroform (10 ml) are dissolved with heating dimethylaminopyridine (0.41 g) and dimethylaminopyridine hydrochloride (0.35 g), and thereto is added N,N-dimethylglycine hydrochloride (0.15 g) at room temperature with stirring, and further added dicyclohexylcarbodiimide (0.46 g). The mixture is stirred at room temperature overnight. To the mixture are added methanol (1.3 ml) and acetic acid (0.4 ml), and the mixture is stirred at room temperature for two hours. Saturated aqueous sodium hydrogen carbonate solution is added to the reaction solution, and the mixture is extracted with dichloromethane, and the extract is dried over magnesium sulfate. The solvent is distilled off under reduced pressure, and the resulting residue is purified by silica gel column chromatography (eluent; methyl acetate), and thereto is added a mixture of hydrochloric acid/methanol. The mixture is stirred at room temperature for one hour to give 5-[(2-dimethylaminoacetyloxy)methyl]-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine hydrochloride (0.36 g) as colorless amorphous.

出典