Reaction #674314

ord-46bdeee1f88d44a59be411178c4965b9

Reaction equation

COC(=O)C(c1ccccc1)C1CCCCN1.Cl
methylphenidate hydrochloride
[NH4+].[OH-]
ammonium hydroxide
COC(=O)C(c1ccccc1)C1CCCCN1
oil
Yield 95.0%
COC(=O)C(c1ccccc1)C1CCCCN1
Methylphenidate
Yield 95.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherformed
  2. 2
    ExtractionThe product was extracted with three 100 mL portions of ethyl acetate
  3. 3
    Dryingthe combined organic layers dried over sodium sulfate
  4. 4
    Filtrationfiltered
  5. 5
    Concentrationconcentrated under reduced pressure at about 40° C.

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09226925B1uspto-grants-2016_01