Sodium borohydride → 1-Benzyl-4-(phenylamino)piperidine-4-methanol

HRID 37372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 37372
[BH4-].[Na+].[C:3]1([NH:9][C:10]2([CH:23]=[O:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO.O>[C:3]1([NH:9][C:10]2([CH2:23][OH:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 19935652HCID 19935652, Verbindung

Produkt 1

HCID 30172301-Benzyl-4-(phenylamino)piperidine-4-methanolAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washthe combined extracts washed
  3. customdried
  4. customAfter removal of the solvent
  5. customthe crude product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3f041f1a149f4c3da5afef44e7d0f088
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420280

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