반응 #336114

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4-(3-piperidinomethylphenoxy)butyronitrile

4-(3-piperidinomethylphenoxy)butyronitrile

LiAlH4

3-piperidinomethylphenol

NaOH

4-chlorobutyronitrile

sodium

→

4-(3-piperidinomethylphenoxy)butaneamine

용매

ether

water

ethanol

ethanol

반응 조건

후처리

1. 1
   온도the batch is heated
2. 2
   온도under reflux overnight with the exclusion of moisture
3. 3
   온도to cool
4. 4
   여과is filtered
5. 5
   농축concentrated to dryness in vacuo
6. 6
   세척washed with 10% NaOH and water
7. 7
   건조Drying over Na2SO4
8. 8
   기타can be used in the subsequent reaction without further purification
9. 9
   온도While cooling with ice
10. 10
    workup.STIRRINGAfter stirring for 40 min at room temperature the batch
11. 11
    workup.STIRRINGStirring
12. 12
    여과the batch is suction-filtered
13. 13
    세척the precipitate is washed several times with ether
14. 14
    세척The filtrate is washed with water
15. 15
    건조dried over Na2SO4
16. 16
    여과filtered
17. 17
    농축concentrated to dryness in vacuo

실험 절차

4.6 g (0.2 mol) of sodium are dissolved in anhydrous ethanol and 38.24 g (0.2 mol) of 3-piperidinomethylphenol [DE-A-2 917 026, Glaxo] are added thereto. After the dropwise addition of 20.71 g (0.2 mol) of 4-chlorobutyronitrile in ethanol, the batch is heated under reflux overnight with the exclusion of moisture. It is then allowed to cool, is filtered, and concentrated to dryness in vacuo. The resulting oil is taken up in ether and washed with 10% NaOH and water. Drying over Na2SO4 and concentrating yield 35.5 g (0.14 mol) of 4-(3-piperidinomethylphenoxy)butyronitrile in the form of an oil that can be used in the subsequent reaction without further purification. While cooling with ice and stirring, 59.9 mmol of 4-(3-piperidinomethylphenoxy)butyronitrile are introduced slowly into a suspension of 2.98 g (78.4 mmol) of LiAlH4 in 140 ml of anhydrous ether. After stirring for 40 min at room temperature the batch is hydrolysed, while cooling with ice, with 10 ml of water-saturated ether and 7 ml of 10% NaOH. Stirring is continued for 30 min, and then the batch is suction-filtered and the precipitate is washed several times with ether. The filtrate is washed with water, dried over Na2SO4, filtered and concentrated to dryness in vacuo to yield 4-(3-piperidinomethylphenoxy)butaneamine in the form of a low-viscosity brown oil that can be used in the subsequent reaction without further purification. The equimolar amount of 4-(3-piperidinomethylphenoxy)butaneamine is added while stirring to a suspension of N-cyanodiphenylimidocarbonate in 100 ml of diethyl ether. After stirring for approx. 15 min, the product, N-cyano-O-phenyl-N'-[4-(3-piperidinomethylphenoxy)butyl]isourea, precipitates copiously, or it crystallises when the solution is concentrated. The product is suction-filtered, washed with diethyl ether and dried.

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