Tetrahydrofuran → HCID 14627460, compound

HRID 2294272Notes

Reaction equation

HRID 2294272 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:3]=1[O:4][CH2:5][CH:6]([NH:8][C:9](=O)[CH3:10])[CH3:7].O1CCCC1>C(O)C.CCOCC>[CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:3]=1[O:4][CH2:5][CH:6]([NH:8][CH2:9][CH3:10])[CH3:7]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 567741Mexiletine acetate

Product 1

HCID 14627460HCID 14627460, compound

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Procedure

Step 2 involves the reduction of the N-[2-(2,6-dimethylphenoxy)-1-methylethyl]-acetamide to the amine. The product from step 1 is heated to reflux temperature in the presence of an aprotic solvent such as tetrahydrofuran, and an effective reducing agent such as borane-dimethylsulfide complex. The reaction temperature is maintained at reflux for about 5-40 hours, preferably about 24 hours, and is preferably performed under an inert atmosphere, e.g., nitrogen. When the reaction is substantially complete, the product is isolated and purified by conventional techniques, for example converting to an acid salt, preferably the hydrochloride salt, then crystallizing from an organic solvent, for example ethanol/ether, yielding racemic [2-(2,6-dimethylphenoxy)-1-methylethyl]-ethylamine salt, preferably the hydrochloride salt.

Workup

  1. temperatureThe reaction temperature is maintained
  2. temperatureat reflux for about 5-40 hours, preferably about 24 hours
  3. customthe product is isolated

Sources & evidence

ORD record
ord-a0dcecfa5a19466993248e62560831b8
Source dataset
uspto-grants-1997_11
Patent number
US05688830

Reaction notes

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