Methane → Hydrocodone

In this Example, 8,14-dihydro-thebaine (6.00 g, 19.14 mmol) was mixed with 50 ml of approx. 2.45 N hydrochloric acid (122.5 mmol, prepared by mixing concentrated hydrochloric acid (10 ml) with DI water (40 ml)) at room temperature with stirring. The homogeneous light yellow colored solution was stirred overnight. Decolorizing charcoal (Darco, 0.3 g) was added to the mixture and the reaction was stirred for 1 hour and then filtered. The charcoal was washed with DI water (2×5 ml). The combined acid phases were cooled to <5° C. and the pH was adjusted to 9.65 with concentrated (28.0-30.0%) ammonium hydroxide solution (approx. 13 ml). The solid was filtered and washed with 2×5 ml of DI water. The product was dried at 60° C. under 22″ Hg vacuum until constant weight to give hydrocodone as a white amorphous solid (5.11 g, 89.2% yield, 96.3 wt % by assay).

1. stirringThe homogeneous light yellow colored solution was stirred overnight
2. stirringthe reaction was stirred for 1 hour
3. filtrationfiltered
4. washThe charcoal was washed with DI water (2×5 ml)
5. temperatureThe combined acid phases were cooled to <5° C.
6. concentrationwith concentrated (28.0-30.0%) ammonium hydroxide solution (approx. 13 ml)
7. filtrationThe solid was filtered
8. washwashed with 2×5 ml of DI water
9. customThe product was dried at 60° C. under 22″ Hg vacuum until constant weight

ORD record

ord-fdba1a2c9a184f02b7aa7d68f0341f33

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399671B2