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

HRID 365369
Notes
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Reaction equation

HRID 365369 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 nitrogen 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 hydrochloric acid 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 nitrogen 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-d41fc18bc94543b09a0d282a80443b10
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06127373

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes