2,6-Dimethylpiperazine → HCID 57809802, compound

HRID 2105987Notes

Reaction equation

HRID 2105987 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[CH3:21][CH:22]1[CH2:27][NH:26][CH2:25][CH:24]([CH3:28])[NH:23]1>CN(C)C=O.C(OCC)C>[CH3:21][CH:22]1[NH:23][CH:24]([CH3:28])[CH2:25][N:26]([CH2:12][C:10]([OH:11])([CH2:9][C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:19][CH3:20])([CH3:18])[CH3:17])[C:13]([F:16])([F:15])[F:14])[CH2:27]1

Participants

5

Reactant 2

HCID 660562,6-DimethylpiperazineHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 57809802HCID 57809802, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (98.7 mg) and 2,6-dimethylpiperazine (77.2 mg) in dimethylformamide (1 mL) was heated at 100° C. for 5 hours. The resulting mixture was diluted with diethyl ether, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 1:98.5:0.5 methanol-methylene chloride-triethylamine) to give the title compound as a white solid (97.3 mg), m.p. 61° C.-62° C.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography with silica gel (eluted with 1:98.5:0.5 methanol-methylene chloride-triethylamine)

Sources & evidence

ORD record
ord-c6fe079748da49cfa7d6c60976ae8535
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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