Reaktion #529240

Reaktionsgleichung

p-toluenesulfonic acid

1-indanone

piperidine

toluene

→

1-(1-Indanyl)piperidine

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 100 g
2. 2
   TemperaturHeating
3. 3
   SonstigeSolvent and excess piperidine are removed in vacuo
4. 4
   workup.DISSOLUTIONthe residue is dissolved in 1500 ml
5. 5
   workup.ADDITIONtreated portionwise with 50 g
6. 6
   Sonstigeof sodium borohydride below 30° C
7. 7
   workup.STIRRINGAfter stirring several hours longer
8. 8
   workup.ADDITIONthe mixture is treated with a small amount of acetic acid
9. 9
   workup.ADDITIONthen made strongly basic by the addition of sodium hydroxide solution
10. 10
    workup.ADDITIONof water is added, most of the methanol
11. 11
    Sonstigeis removed in vacuo
12. 12
    ExtraktionProduct is extracted into ether
13. 13
    Trocknendried over potassium hydroxide
14. 14
    workup.DISTILLATIONdistilled
15. 15
    Sonstigeof 1-(1-indanyl)piperidine is collected at 101°-102° (0.2 mm.)

Vorschrift

A mixture of 100 g. of 1-indanone (0.758 mole) and 125 ml. of piperidine in 750 ml. of toluene is treated with 0.5 g. of p-toluenesulfonic acid and heated under reflux with a water take-off trap attached. Heating is continued for 48 hours. Solvent and excess piperidine are removed in vacuo and the residue is dissolved in 1500 ml. of absolute methanol. The resulting solution is stirred and treated portionwise with 50 g. of sodium borohydride below 30° C. After stirring several hours longer, the mixture is treated with a small amount of acetic acid then made strongly basic by the addition of sodium hydroxide solution. After 400 ml. of water is added, most of the methanol is removed in vacuo. Product is extracted into ether, dried over potassium hydroxide and distilled. 119.7 g. of 1-(1-indanyl)piperidine is collected at 101°-102° (0.2 mm.).

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