반응 #933006

반응 방정식

naloxone hydrochloride

O-methylhydroxylamine hydrochloride

MeOH

NaOH

→

6-Methyloximino-17-allyl-4,5α-epoxy-3,14-dihydroxymorphinan

용매

water

반응 조건

후처리

1. 1
   온도the mixture was refluxed for 5 h
2. 2
   온도It was cooled
3. 3
   추출extracted with 150 mL CHCl3 (3×50 mL)
4. 4
   건조The combined extracts were dried (MgSO4)
5. 5
   기타evaporated
6. 6
   기타The residue obtained
7. 7
   기타was recrystallized from hexane-petroleum ether
8. 8
   기타IR (KBr): No C=O absorption at 1717 cm-1

실험 절차

A solution of naloxone hydrochloride (1.09 g, 3 mmol) and O-methylhydroxylamine hydrochloride (0.33 g, 3.9 mmol) in 15 mL MeOH was stirred overnight. After the addition of 3.2 mL of 10% aqueous NaOH, the mixture was refluxed for 5 h. It was cooled, diluted with approx. 100 mL of water, and extracted with 150 mL CHCl3 (3×50 mL). The combined extracts were dried (MgSO4) and evaporated. The residue obtained was recrystallized from hexane-petroleum ether. Yield 0.8 g, (75%) mp 128-129° C. IR (KBr): No C=O absorption at 1717 cm-1 ; H NMR (CDCl3): δ4.95 (s, C5H), 3.82 (s, OCH3). Rf: silica gel 60 in EtOAc-EtOH-NH4OH (100:1:1) 0.50. Anal. Calcd for C20H24N2O4 : C, 67.40; H, 6.79; N, 7.86. Found: C, 67.27; H, 6.84; N, 7.82.

출처