1-Methylpiperazine → HCID 135444737, compound

HRID 915923Notes

Reaction equation

HRID 915923 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[NH:35][C:36](=[O:50])[C:37]3[C:42]([CH:43]4[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]4)=[N:41][N:40]([CH3:49])[C:38]=3[N:39]=2)=[C:30]([O:51][CH3:52])[CH:29]=1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH:43]1([C:42]2[C:37]3[C:36](=[O:50])[NH:35][C:34]([C:31]4[CH:32]=[CH:33][C:28]([N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[CH:29][C:30]=4[O:51][CH3:52])=[N:39][C:38]=3[N:40]([CH3:49])[N:41]=2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 136005920HCID 136005920, compound

Product 1

HCID 135444737HCID 135444737, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a stream of argon, 207 μl (1.87 mmol) of N-methylpiperazine, 120 mg (1.25 mmol) of sodium tert-butoxide, 12.6 mg (0.062 mmol) of tri-tert-butylphosphine, and 7.0 mg (0.031 mmol) of palladium(II) acetate were added to an 8 ml toluene solution of 260 mg (0.623 mmol) of the compound obtained in Example 26, and the mixture was heated under reflux for 5 hours. Then, the reaction mixture was brought to room temperature, diluted with water, and then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=20/1) to obtain 230 mg (85%) of the captioned compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customwas brought to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-84b2acaf0f9a4d02a35a3e475aad9af9
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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