反応 #570787

反応方程式

sodium nitrite

hydrochloric acid

1-[3-(4-cyanophenoxy)propyl]-4diphenylmethoxypiperidine

ammonium chloride

sodium azide

→

1-{3-[4-(1,2,3,4-tetrazol-5-yl)phenoxy]propyl)-4-diphenylmethoxypiperidine

収率 65.2%

溶媒

water

n-hexane

water

dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at 100° C. to 110° C. for 12 hours
2. 2
   その他After completion of the reaction
3. 3
   温度to cool to 70° C.
4. 4
   workup.ADDITIONwas added
5. 5
   温度to cool to 35° C.
6. 6
   その他to give vigorous gas evolution
7. 7
   その他After the supernatant was removed by decantation, 50 ml of ethyl acetate
8. 8
   workup.ADDITIONwas added to the residual amber viscous product
9. 9
   workup.STIRRINGthe mixture was shaken vigorously
10. 10
    洗浄washed sufficiently with ethyl acetate

実験手順

1.67 g (3.92 mmol) of 1-[3-(4-cyanophenoxy)propyl]-4diphenylmethoxypiperidine dissolved in 15 ml of dimethylformamide was added 1.26 g (23.6 mmol) of ammonium chloride, and the mixture was stirred at 45° C. for 15 minutes. Subsequently, 1.02 g (15.7 mmol) of sodium azide was added to the mixture, and the mixture was stirred at 100° C. to 110° C. for 12 hours. After completion of the reaction, the reaction mixture was allowed to cool to 70° C., and a solution of 1.6 ml of conc. hydrochloric acid diluted with 50 ml of water was added. After the mixture was allowed to cool to 35° C., 10 ml of n-hexane and 1.35 g (19.6 mmol) of sodium nitrite in 5 ml of water were added to the mixture to give vigorous gas evolution and then an amber viscous product was liberated. After the supernatant was removed by decantation, 50 ml of ethyl acetate was added to the residual amber viscous product, and the mixture was shaken vigorously. The precipitated crystals were filteref off and washed sufficiently with ethyl acetate to obtain 1.20 g (yield: 65%) of 1-{3-[4-(1,2,3,4-tetrazol-5-yl)phenoxy]propyl)-4-diphenylmethoxypiperidine as pale brown crystals.

出典