Water → HCID 9843069, compound

HRID 2105252Notes

Reaction equation

HRID 2105252 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:8][CH:7]=1)=[O:4].[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C([O-])([O-])=O.[K+].[K+].O>CC#N>[CH2:14]([CH:13]([CH2:16][CH3:17])[CH:12]([C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)=[CH:7][CH:8]=1)[N:18]1[CH:22]=[N:21][CH:20]=[N:19]1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 22335514HCID 22335514, compound

Product 1

HCID 9843069HCID 9843069, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (±)-2-chloro-N-[4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl]acetamide (0.0218 mol), 1-methylpiperazine (0.0436 mol) and K2CO3 (0.0436 mol) in CH3CN (150 ml) was stirred and refluxed for 4 hours. The mixture was cooled, poured out into water and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue (8.13 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 3 g (35.8%) (±)—N-[4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl]-4-methyl-1-piperazineacetamide (compound 15).

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with CH2Cl2
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue (8.13 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.5)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from diethyl ether
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-549449e7fe764abbb35f9f664a33a3cd
Source dataset
uspto-grants-2009_08
Patent number
US07579352B2

Reaction notes

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