Diisopropylethylamine → t-Butyl 4-(4-cyano-3-trifluoromethylphenyl)-3-methylpiperazine-1-carboxylate

HRID 1838230Notes

Reaction equation

HRID 1838230 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([N:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][CH:2]2[CH3:1])=[CH:17][C:18]=1[C:24]([F:25])([F:26])[F:27])#[N:21]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 4.46 g portion of t-butyl 3-methylpiperazine-1-carboxylate synthesized in Reference Example 2, 6.74 g of 4-fluoro-2-trifluoromethylbenzonitrile and 7.76 ml of diisopropylethylamine were stirred in 50 ml of DMF at 100° C. for 2 days. The reaction solution was diluted with water and extracted with ethyl acetate, the organic layer was washed and dried and then the solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (3:1, v/v) to obtain 5.6 g of the title compound as white crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. washeluted with hexane-ethyl acetate (3:1

Sources & evidence

ORD record
ord-3c5e870a547c475ab45cc77f837214aa
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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