Reaktion #1243741

Reaktionsgleichung

n-Heptylamine

4-(4-nitrophenyl)butanoyl chloride

N-n-heptyl-4-(4-nitrophenyl)butyramide

N-n-heptyl-4-(4-nitrophenyl)butylamine

diborane

acetyl chloride

sodium carbonate

→

N-acetyl-N-n-heptyl-4-(4-nitrophenyl)butylamine

Lösungsmittel

water

acetone

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto provide 29.3 g
2. 2
   Sonstigeto afford 25.8 g
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature for sixteen hours
4. 4
   workup.ADDITIONthe addition
5. 5
   Einengenthe mixture was concentrated by evaporation of the acetone solvent under reduced pressure
6. 6
   ExtraktionThe aqueous layer was extracted with diethyl ether
7. 7
   Extraktionthe ethereal extract
8. 8
   Waschenwas then washed with water, with 2 N hydrochloric acid, again with water
9. 9
   SonstigeThe solution was dried
10. 10
    Sonstigethe solvent was removed by evaporation under reduced pressure

Vorschrift

n-Heptylamine was reacted with 4-(4-nitrophenyl)butanoyl chloride to provide 29.3 g. of N-n-heptyl-4-(4-nitrophenyl)butyramide. The amide was reacted with diborane to afford 25.8 g. of N-n-heptyl-4-(4-nitrophenyl)butylamine. The amine was dissolved in 70 ml. of acetone and added in one portion to 70 ml. of water containing 18.5 g. of sodium carbonate. The aqueous reaction mixture was stirred while 14.4 ml. of acetyl chloride in 70 ml. of acetone was added dropwise over one hour. The reaction mixture was stirred at room temperature for sixteen hours following the addition, and then the mixture was concentrated by evaporation of the acetone solvent under reduced pressure. The aqueous layer was extracted with diethyl ether, and the ethereal extract was then washed with water, with 2 N hydrochloric acid, again with water, and finally with saturated sodium chloride solution. The solution was dried and the solvent was removed by evaporation under reduced pressure to give 28.78 g of N-acetyl-N-n-heptyl-4-(4-nitrophenyl)butylamine.

Quelle