Hydrochloric Acid → 5-(2-(4-(1-Naphthyl)piperazinyl)ethyl)oxindole

HRID 1639272Notes

Reaction equation

HRID 1639272 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2.Cl.[C:15]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl>CCOCC.CC(CC(C)C)=O>[C:15]1([N:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][C:4]3[CH:5]=[C:6]4[C:10](=[CH:11][CH:12]=3)[NH:9][C:8](=[O:13])[CH2:7]4)[CH2:27][CH2:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 27373911-(1-Naphthyl)piperazine hydrochlorideHCID 145813925-(2-Chloroethyl)Oxindole

Product 1

HCID 111761995-(2-(4-(1-Naphthyl)piperazinyl)ethyl)oxindole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 50 ml round bottomed flask equipped with condenser and N2 inlet were added 370 mg (1.69 mmol) 5-(2-chloroethyl)oxindole, 400 mg (1.69 mmol) N-(1-naphthyl)piperazine hydrochloride, 200 mg (1.69 mmol) sodium carbonate, 2 mg sodium iodide, and 50 ml methylisobutylketone. The reaction was refluxed 24 hours, cooled, and evaporated. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel with ethyl acetate, and the product fractions collected and evaporated to give a foam. The foam was dissolved in ether, treated with HCl gas, and the precipitate collected, washed with ether, and dried to afford a white solid, m.p. 303°-305° C., 603 mg (84%).

Workup

  1. customTo a 50 ml round bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 24 hours
  3. temperaturecooled
  4. customevaporated
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with ethyl acetate
  9. customthe product fractions collected
  10. customevaporated
  11. customto give a foam
  12. customthe precipitate collected
  13. washwashed with ether
  14. customdried
  15. customto afford a white solid, m.p. 303°-305° C., 603 mg (84%)

Sources & evidence

ORD record
ord-af76d5f50ad547de9800d368c34a3463
Source dataset
uspto-grants-1989_11
Patent number
US04883795

Reaction notes

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