Potassium Carbonate → HCID 9819770, compound

HRID 2287991Notes

Reaction equation

HRID 2287991 reaction equation
S([CH2:11][CH2:12][CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[NH:14]1)(C1C=CC(C)=CC=1)(=O)=O.[CH3:23][C:24]1[CH:25]=[C:26]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:27]=[CH:28][C:29]=1[CH3:30].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:23][C:24]1[CH:25]=[C:26]([N:31]2[CH2:32][CH2:33][N:34]([CH2:11][CH2:12][CH:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[NH:14]3)[CH2:35][CH2:36]2)[CH:27]=[CH:28][C:29]=1[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27237821-(3,4-Xylyl)piperazineHCID 18703635HCID 18703635, compound

Product 1

HCID 9819770HCID 9819770, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,3-dihydro-3-(2-tosylethyl)-2H-isoindol-1-one (4.2 g, 12.7 mmol), 1-(3,4-dimethylphenyl)-piperazine (2.6 g, 13.9 mmol), and K2CO3 (8.8 g, 63.3 mmol) in 150 mL of CH3CN is warmed to reflux overnight under argon. After being cooled to room temperature, the solvent is evaporated, and the remaining solid is stirred in 100 mL of H2O for 20 minutes. The solid is collected, dried, and recrystallized from CH3CN to give 2.7 g (60% yield) of 3-{2-[4-(3,4-dimethyl-phenyl)-piperazin-1-yl]-ethyl}-2,3-dihydro-isoindol-1-one; mp=167-169° C.

Workup

  1. temperatureto reflux overnight under argon
  2. customthe solvent is evaporated
  3. customThe solid is collected
  4. customdried
  5. customrecrystallized from CH3CN

Sources & evidence

ORD record
ord-97a44e6c808d438dac7de5b3c3872e89
Source dataset
uspto-grants-2000_07
Patent number
US06087364

Reaction notes

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