Methylphenidate Hydrochloride → Dexmethylphenidate

HRID 1850041Notes

Reaction equation

HRID 1850041 reaction equation
[CH3:1][O:2][C:3]([CH:5]([CH:12]1[NH:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:4].Cl.[OH-].[NH4+]>O>[CH3:1][O:2][C:3]([C@H:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C@@H:12]1[NH:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:4]

Participants

4

Reactant 2

HCID 9280Methylphenidate HydrochlorideHCID 14923Ammonium Hydroxide

Product 1

HCID 154101DexmethylphenidateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 200 mL beaker was charged 10.0 g (37.1 mmol) racemic-methylphenidate hydrochloride and 135 mL water. Ammonium hydroxide (3.40 g; 96.8 mmol) was then added to bring the pH to approximately 9 upon which an oily semi-solid formed. The product was extracted with three 100 mL portions of ethyl acetate, the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduce pressure at 40° C. to provide 8.5 g of a clear, colorless viscous oil (98% yield). The free base was characterized by FTIR and found to be consistent with the anticipated structure

Workup

  1. customformed
  2. extractionThe product was extracted with three 100 mL portions of ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customat 40° C.

Sources & evidence

ORD record
ord-ef69523275dd41cda32fc1bed59e3fa7
Source dataset
uspto-grants-2015_02
Patent number
US08957067B1

Reaction notes

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