t-Butyl 4-(4-cyano-3-trifluoromethylphenyl)-3-methylpiperazine-1-carboxylate → 4-(2-Methylpiperazin-1-yl)-2-trifluoromethylbenzonitrile

HRID 1838231Notes

Reaction equation

HRID 1838231 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH:10]2[CH3:22])=[CH:5][C:4]=1[C:23]([F:26])([F:25])[F:24])#[N:2]>FC(F)(F)C(O)=O>[CH3:22][CH:10]1[CH2:11][NH:12][CH2:13][CH2:14][N:9]1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:23]([F:26])([F:24])[F:25])[CH:5]=1

Participants

3

Reactant 1

HCID 18753316t-Butyl 4-(4-cyano-3-trifluoromethylphenyl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 113231584-(2-Methylpiperazin-1-yl)-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A 2.85 g portion of t-butyl 4-(4-cyano-3-trifluoromethylphenyl)-3-methylpiperazine-1-carboxylate synthesized in Reference Example 3 was stirred in 50 ml of trifluoroacetic acid at 0° C. to room temperature for 2 hours. The solvent was evaporated under reduced pressure, the resulting residue was neutralized with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate, the organic layer was washed and dried and then the solvent was evaporated under reduced pressure. The residue was purified by a silica gel column chromatography, and 5.6 g of the title compound was obtained from chloroform-methanol-28% aqueous ammonia (10:1:0.1, v/v/v) eluate as light yellowish white crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-2ec50541866649f8a4a69cb2829d1dfd
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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