Methylphenidate Hydrochloride → Methylphenidate

HRID 1406030Notes

Reaction equation

HRID 1406030 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]([CH:5]([CH:12]1[NH:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 9280Methylphenidate HydrochlorideHCID 14923Ammonium Hydroxide

Product 1

HCID 4158MethylphenidateYield 95%

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. About 3.39 g (96.8 mmol) ammonium hydroxide 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 dried over sodium sulfate, filtered and concentrated under reduced pressure at about 40° C. to provide 8.2 g of a clear, colorless viscous oil (95% yield). The IR spectrum of the oil was consistent with the intended product.

Workup

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

Sources & evidence

ORD record
ord-6a7b6c11becf4e1d9ddc2aaf4b16e0e3
Source dataset
uspto-grants-2014_12
Patent number
US08916587B1

Reaction notes

Loading…