Methylphenidate Hydrochloride → Methylphenidate

HRID 2041955Notes

Reaction equation

HRID 2041955 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-d5595930174447e897d5f1d2fd4f4287
Source dataset
uspto-grants-2013_11
Patent number
US08586575B1

Reaction notes

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