Hydrochloric Acid → Oxycodone Hydrochloride

HRID 1436848Notes

Reaction equation

HRID 1436848 reaction equation
[ClH:1].[CH3:2][N:3]1[C@@H:20]2[CH2:21][C:8]3[CH:9]=[CH:10][C:11]([O:23][CH3:24])=[C:12]4[O:13][C@H:14]5[C:15]([CH2:17][CH2:18][C@:19]2([OH:22])[C@:6]5([C:7]=34)[CH2:5][CH2:4]1)=[O:16]>>[CH3:2][N:3]1[C@@H:20]2[CH2:21][C:8]3[CH:9]=[CH:10][C:11]([O:23][CH3:24])=[C:12]4[O:13][C@H:14]5[C:15]([CH2:17][CH2:18][C@:19]2([OH:22])[C@:6]5([C:7]=34)[CH2:5][CH2:4]1)=[O:16].[ClH:1]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 5284603Oxycodone

Product 1

HCID 5462350Oxycodone HydrochlorideYield 95.6%

Conditions

Temperature
2 °C

Procedure

An aqueous solution of HCl (87.0 kg of water and 13.00 kg of conc. HCl) is stirred with 48 kg of Oxycodone base at 80° C., activated carbon and diatomaceous earth are added and, after stirring for 15 min, the suspension is filtered, the filtrate is gradually cooled down to the final temperature of 1 to 3° C. Precipitated crystals are centrifuged off, washed with ethanol, and Oxycodone hydrochloride is dried at temperature of about 70 to 80° C. 51.2 kg of (91%) Oxycodone hydrochloride is obtained, m.p. 219° C, [α]D2°—145°, water content 6.0%, purity 99.4% (RP C8 column, 150×3.9 mm, 5 μm, with a RP C8 pre-column, 20×3.9 mm, 5 μm, mobile phase 0.005 mol/l sodium hexane sulfonate-methanol-phosphoric acid-triethyl-amine (v/v) (900:100:5:2), pH=2.5 adjusted with NaOH; flow rate 1.5 ml/min; temperature 50° C.; UV, λ=206 run), content 100.03% (titration).

Workup

  1. additionactivated carbon and diatomaceous earth are added
  2. filtrationthe suspension is filtered
  3. customPrecipitated crystals
  4. washwashed with ethanol, and Oxycodone hydrochloride
  5. customis dried at temperature of about 70 to 80° C

Sources & evidence

ORD record
ord-d4ddd49867a74b63b91a642606285a0b
Source dataset
uspto-grants-2009_11
Patent number
US07619087B2

Reaction notes

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