反応 #54453

反応方程式

hydrochloric acid

γ-(4-benzyl-4-hydroxypiperidino)-2-aminobutyrophenone

sodium nitrite

hydrochloric acid

→

γ-(4-benzyl-4-hydroxypiperidino)-2-chlorobutyrophenone hydrochloride

溶媒

water

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred for 30 minutes
2. 2
   温度under cooling with ice
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITfor 1 hour at 55°-60° C
5. 5
   温度After cooling
6. 6
   抽出extracted with chloroform
7. 7
   洗浄The extract was washed with water
8. 8
   その他dried
9. 9
   濃縮concentrated to a residue
10. 10
    workup.ADDITIONThe residue was treated with methanolic hydrogen chloride and recrystallization of the resulting solid matter from isopropanol

実験手順

To a cooled solution of 3.6 g of γ-(4-benzyl-4-hydroxypiperidino)-2-aminobutyrophenone in 35 ml of 2N hydrochloric acid was added dropwise a solution of 0.74 g of sodium nitrite in 5 ml of water with stirring below 0° C. The resulting diazonium salt solution was added all at once to a cold suspension of 1.5 g of cuprous chloride in 5 ml of concentrated hydrochloric acid with vigorous stirring. The mixture was stirred for 30 minutes under cooling with ice, and stirring was continued for 2 hours at room temperature and then for 1 hour at 55°-60° C. After cooling, the reaction mixture was made alkaline, and extracted with chloroform. The extract was washed with water, dried and concentrated to a residue. The residue was treated with methanolic hydrogen chloride and recrystallization of the resulting solid matter from isopropanol gave γ-(4-benzyl-4-hydroxypiperidino)-2-chlorobutyrophenone hydrochloride.8c

出典