Reaktion #65650

Reaktionsgleichung

Sodium borohydride

4-(N-phenylamino)-1-phenylmethyl-piperidine-4-carboxaldehyde

→

title compound

Ausbeute 76.0%

4-(N-phenylamino)-1-phenylmethyl-4-piperidinylmethanol

Ausbeute 76.0%

Lösungsmittel

water

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with chloroform
2. 2
   Waschenthe combined extracts washed
3. 3
   Sonstigedried
4. 4
   SonstigeAfter removal of the solvent
5. 5
   Sonstigethe crude product was purified by chromatography on silica gel

Vorschrift

Sodium borohydride (2 g) was added portionwise to a stirred solution of 4-(N-phenylamino)-1-phenylmethyl-piperidine-4-carboxaldehyde (2 g) in methanol at room temperature. After stirring at room temperature for 2 hours the mixture was diluted with water, extracted with chloroform and the combined extracts washed and dried. After removal of the solvent, the crude product was purified by chromatography on silica gel, using chloroform/methanol (38:1) as eluant, to give the title compound (1.53 g) 4-(N-phenylamino)--1-phenylmethyl-4-piperidinylmethanol is then converted to sufentanil following the method described in U.S. Pat. No. 4,179,469 and as illustrated by FIG. 2.

Quelle