Reaktion #74807

Reaktionsgleichung

sodium cyanoborohydride

1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride

hydrochloric acid

heptaldehyde

→

1-[2-(N-isopropyl-N-heptylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Lösungsmittel

acetonitrile

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   workup.ADDITIONmixture of 5.0 g
3. 3
   Temperaturcooled
4. 4
   Sonstigeevaporated
5. 5
   Sonstigeto remove the acetonitrile
6. 6
   workup.ADDITIONThe residue is diluted with water
7. 7
   Waschenthe solution washed with diethyl ether
8. 8
   Extraktionextracted with chloroform
9. 9
   SonstigeThe extract is dried
10. 10
    Sonstigeevaporated
11. 11
    Sonstigethe residue crystallized from ethanol-water (5:2)

Vorschrift

2.66 ml of glacial acetic acid are added dropwise to the ice-cooled mixture of 5.0 g of slow moving 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride, 15.2 g of heptaldehyde, 2.52 g of sodium cyanoborohydride and 53 ml of acetonitrile. The mixture is stirred at room temperature for 2 hours, cooled, acidified to pH=1 with concentrated hydrochloric acid and evaporated to remove the acetonitrile. The residue is diluted with water, the solution washed with diethyl ether, basified to pH=10-11 with 3 N aqueous sodium hydroxide and extracted with chloroform. The extract is dried, evaporated and the residue crystallized from ethanol-water (5:2) to give the 1-[2-(N-isopropyl-N-heptylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, RR racemate melting at 102°-104°.

Quelle