Sodium Bicarbonate → Hydrocodone

HRID 589422Notes

Reaction equation

HRID 589422 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].C(O)(C(O)=O)C(O)C(O)=O.C([O-])(O)=O.[Na+]>O>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20831824(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;2,3-dihydroxybutanedioic acid

Product 1

HCID 5284569Hydrocodone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydrocodone bitartrate salt was dissolved in water. To this was added 2 equivalents solid NaHCO3. Hydrocodone precipitates and dichlormethane was added. The biphasic solution was allowed to stir for twenty minutes. The layers were then separated and the basic aqueous layer was extracted two times with dichloromethane. The organic layer was dried over MgSO4 and evaporated to yield hydrocodone free base as a white powder. Isolated yield was generally 95+%

Workup

  1. customHydrocodone precipitates
  2. additiondichlormethane was added
  3. customThe layers were then separated
  4. extractionthe basic aqueous layer was extracted two times with dichloromethane
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-e7182cec74e14271a01f85e0cfdb077b
Source dataset
uspto-grants-2016_01
Patent number
US09233168B2

Reaction notes

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