Methylphenidate Hydrochloride → HCID 86730903, compound

HRID 1525133Notes

Reaction equation

HRID 1525133 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.Cl[C:20]([O:22][CH2:23][Cl:24])=[O:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:20]([O:22][CH2:23][Cl:24])=[O:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 9280Methylphenidate HydrochlorideHCID 62754Chloromethyl chloroformate

Product 1

HCID 86730903HCID 86730903, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methylphenidate hydrochloride (1) (2.70 g, 10 mmol) was suspended in DCM (75 mL) and cooled in an ice bath. 4-Dimethylaminopyridine (DMAP) (4.887 g, 40 mmol) was added and the resulting mixture was stirred for 10 min. Chloromethyl chloroformate (3.224 g, 25 mmol) in DCM (10 mL) was added slowly. The ice bath was removed and the reaction was stirred for 5 h at room temperature. Ethyl acetate (250 mL) was added, followed by water (20 mL) to quench the reaction. The ethyl acetate layer was separated and washed with 1N HCl (40 mL) and brine (2×40 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexanes:EtOAc, 3:1) to give 37 as a colorless oil (2.60 g) (yield, 80%).

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice bath was removed
  3. stirringthe reaction was stirred for 5 h at room temperature
  4. additionEthyl acetate (250 mL) was added
  5. customto quench
  6. customthe reaction
  7. customThe ethyl acetate layer was separated
  8. washwashed with 1N HCl (40 mL) and brine (2×40 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated
  11. customthe residue was purified by silica gel column chromatography (hexanes:EtOAc, 3:1)

Sources & evidence

ORD record
ord-90d64ece0c6b4536b6834b8fe2578db8
Source dataset
uspto-grants-2015_07
Patent number
US09079928B2

Reaction notes

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