Reaktion #56437

Reaktionsgleichung

ethyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate

sodium hydroxide

→

4-(phenylamino)-1-(phenylmethyl)-4-piperidinemethanol

Lösungsmittel

benzene

benzene

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGUpon completion, stirring
2. 2
   Sonstigeat 80° C
3. 3
   TemperaturThe reaction mixture is cooled
4. 4
   workup.ADDITIONpoured onto ice-water
5. 5
   Extraktionthe product is extracted with benzene
6. 6
   WaschenThe extract is washed twice with water
7. 7
   Sonstigedried
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated
10. 10
    FiltrationThe salt is filtered off
11. 11
    Temperaturafter cooling
12. 12
    Filtrationthe product is filtered off
13. 13
    Filtrationis filtered off again
14. 14
    Temperaturafter cooling
15. 15
    ExtraktionAfter extraction with 1.1'-oxybisethane
16. 16
    Waschenthe latter is washed with water
17. 17
    Sonstigedried
18. 18
    Sonstigeevaporated

Vorschrift

To a stirred and refluxing solution of 101.4 parts of ethyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate in 640 parts of dry benzene is added dropwise a solution of 172 parts of a sodium dihydro-bis(2-methoxyethoxy)aluminate 70% in benzene, in 160 parts of dry benzene. Upon completion, stirring is continued for 21 h.30 at 80° C. The reaction mixture is cooled, poured onto ice-water, alkalized with sodium hydroxide soltuion and the product is extracted with benzene. The extract is washed twice with water, dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanol and 1.1'-oxybisethane. The salt is filtered off, boiled in 2-propanol and after cooling, the product is filtered off. It is boiled once more in acetronitrile and the salt is filtered off again after cooling. The free base is liberated in the conventional manner. After extraction with 1.1'-oxybisethane, the latter is washed with water, dried and evaporated, yielding 56.6 parts of 4-(phenylamino)-1-(phenylmethyl)-4-piperidinemethanol as an oily residue.

Quelle