Hydrochloric Acid → Oxycodone Hydrochloride

HRID 557155

Reaktionsgleichung

Reaktionsgleichung von HRID 557155
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].CN1[C@@H]2CC3C=CC(OC)=C4OC5C(C=C[C@]2(O)[C@]5(C=34)CC1)=O.O.[ClH:48]>C(O)CCC.[Zn]>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].[ClH:48]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5284603OxycodoneHCID 5359420(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

Produkt 1

HCID 5462350Oxycodone Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Oxycodone base (40.07 g) containing 4869 ppm of 14-hydroxycodeinone and 13.7 ppm DHDHC, was suspended in 1-butanol (250 mL) and water (180 mL) in a jacketed reactor. At 15° C. and with the reaction under nitrogen, aqueous hydrochloric acid (37%) was added to achieve a pH of 2.86. At 25° C., zinc dust (1 g) was added and the resulting mixture was stirred for 3 hr (Note: pH increased to ˜5.86 upon zinc powder addition). Activated carbon (Norit KB-G, 4 g) was added to the reactor and the solution was allowed to stir for 40 min. The reaction mixture was then filtered to remove the zinc and carbon. The filtrate was charged to a clean reactor. The pH of the solution was adjusted to 6.17 using pyridine (15 mL). Water was distilled off under vacuum at 60° C. The solution was then cooled to 20° C. and allowed to stir for 15 min. The solids were filtered and washed with 1-butanol (20 mL×2). The product was dried to a constant weight at ˜65° C. under vacuum to yield 42.14 g of crude oxycodone hydrochloride.

Aufarbeitung

  1. customAt 15° C. and with the reaction under nitrogen
  2. additionActivated carbon (Norit KB-G, 4 g) was added to the reactor
  3. stirringto stir for 40 min
  4. filtrationThe reaction mixture was then filtered
  5. customto remove the zinc and carbon
  6. additionThe filtrate was charged to a clean reactor
  7. distillationWater was distilled off under vacuum at 60° C
  8. stirringto stir for 15 min
  9. filtrationThe solids were filtered
  10. washwashed with 1-butanol (20 mL×2)
  11. customThe product was dried to a constant weight at ˜65° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d2e9d904570c4a5280a0f6fdb95662eb
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058439B2

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