Trimethylamine → HCID 13649190, compound

HRID 648980Notes

Reaction equation

HRID 648980 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([OH:3])=O.CN(C)C.C(OP(Cl)(OCC)=O)C.[CH2:27]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[CH2:27]([N:34]1[CH2:39][CH2:38][N:37]([C:1]([C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[CH2:7]3)=[O:3])[CH2:36][CH2:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 13139Diethyl chlorophosphateHCID 759941-BenzylpiperazineHCID 27733182-Oxindole-5-carboxylic acid

Product 1

HCID 13649190HCID 13649190, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

5-Carboxyoxindol (0.93 g) and 0.8 ml of trimethylamine were suspended in 10 ml of tetrahydrofuran (THF), and a solution of 1.0 g of diethylchlorophosphate in 10 ml of THF was added dropwise thereto at room temperature with stirring. The mixture was stirred for 3 hours at room temperature. To the mixture was added dropwise a solution of 1.1 g of benzylpiperazine in 10 ml of THF and was further stirred for 10 hours at room temperature. After completion of reaction, crystals which precipitated were filtered off and the filtrate was concentrated. To the residue was added a saturated aqueous solution of sodium hydrogencarbonate and the mixture was extracted with chloroform. Organic layer was washed with water and a saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled off. Recrystallization of the residue from isopropyl alcohol gave 1.01 g of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol.

Workup

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. stirringwas further stirred for 10 hours at room temperature
  3. customAfter completion of reaction, crystals which
  4. customprecipitated
  5. filtrationwere filtered off
  6. concentrationthe filtrate was concentrated
  7. additionTo the residue was added a saturated aqueous solution of sodium hydrogencarbonate
  8. extractionthe mixture was extracted with chloroform
  9. washOrganic layer was washed with water
  10. dry with materiala saturated saline solution, dried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off
  12. customRecrystallization of the residue from isopropyl alcohol

Sources & evidence

ORD record
ord-1f42e14d392f4ad1bbe108c5e3bb8488
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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