Mexiletine → Mexiletine acetate

HRID 2294271Notes

Reaction equation

HRID 2294271 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[O:4][CH2:5][CH:6]([NH2:8])[CH3:7].CC1[C:20]([O:21]CC(N)C)=[C:19](C)C=CC=1.C(N)(=O)C.C(Cl)(=O)C.C(OC(=O)C)(=O)C>C(OCC)(=O)C>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[O:4][CH2:5][CH:6]([NH:8][C:20](=[O:21])[CH3:19])[CH3:7]

Participants

6

Reactant 4

HCID 4178Mexiletine2×HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 67701997HCID 67701997, compound

Product 1

HCID 567741Mexiletine acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In Step 1, 2-(2,6-dimethylphenoxy)-1-methyl-ethylamine (mexiletine) is converted to mexiletine acetamide. Mexiletine is treated with an acetylating agent, such as an acetyl chloride or acetic anhydride, in the presence of concentrated aqueous alkali and an organic solvent, e.g., ethyl acetate. The reaction temperature is maintained at about 0°-25° C., preferably below 10° C., for about 10 minutes to 3 hours, preferably about 35 minutes. Following completion of the reaction, the resulting N-[2-(2,6-dimethylphenoxy)-1-methylethyl]-acetamide is isolated by conventional techniques, and used as such in Step 2.

Workup

  1. temperatureThe reaction temperature is maintained at about 0°-25° C., preferably below 10° C., for about 10 minutes to 3 hours, preferably about 35 minutes
  2. customcompletion of the reaction

Sources & evidence

ORD record
ord-8d671e650dfa4e4b80688111e6b099e7
Source dataset
uspto-grants-1997_11
Patent number
US05688830

Reaction notes

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