Maleic Acid → 4-[2-[4-(1H-indole-3-yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone maleate

HRID 2209970Notes

Reaction equation

HRID 2209970 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20](=[O:28])[CH:19]=3)[CH2:12][CH2:11]2)=[CH:2]1.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33]>CO.O1CCCC1>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20](=[O:28])[CH:19]=3)[CH2:12][CH2:11]2)=[CH:2]1

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 3073949Swr 00151

Product 1

HCID 677852834-[2-[4-(1H-indole-3-yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone maleateYield 61.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[2-[4-(1H-indole-3-yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone (III-2) (500 mg, 1.35 mmol) in methanol (15 ml) and tetrahydrofuran (25 ml) was refluxed until solids were dissolved. Under the same conditions, maleic acid (172.9 mg, 1.49 mmol) in methanol (10 ml) was added thereto and then the solvent was distilled off from the reaction mixture. The residue was crystallized with acetone and then recrystallized from acetone-methanol to give the desired product (III'-2-b) (404 mg) as pale yellow crystals (138°-141 ° C., yield 61.4%)

Workup

  1. temperaturewas refluxed until solids
  2. dissolutionwere dissolved
  3. distillationthe solvent was distilled off from the reaction mixture
  4. customThe residue was crystallized with acetone
  5. customrecrystallized from acetone-methanol

Sources & evidence

ORD record
ord-e6cdfea81df74dbd95e854fb494ab13f
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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