Water → HCID 645096, compound

HRID 1358603Notes

Reaction equation

HRID 1358603 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26].O>O1CCCC1.ClCCl>[CH3:26][C:25]([CH3:28])([CH3:27])[C:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1)=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 7372534-(4-Methylpiperazin-1-yl)aniline

Product 1

HCID 645096HCID 645096, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.58 g (29 mmol) 1-(4-aminophenyl)-4-methylpiperazine and 3.77 g (29 mmol) N-ethyldiisopropylamine in 30 ml tetrahydrofuran was cooled in an ice bath and 3.518 g (29 mmol) pivaloyl chloride were added dropwise. The suspension was stirred for 18 h at room temperature. Water (30 ml) and dichloromethane (50 ml) were added and the organic layer was separated. The aqueous phase was re-extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate) and evaporated to give a white solid. Washing with a mixture of hexane and ethyl acetate (4:1) yielded 6.69 g (83%) of a white crystalline compound.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous phase was re-extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. customevaporated
  5. customto give a white solid
  6. washWashing with a mixture of hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-a2d8d691167f4b948cba2b264986dece
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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