Sodium Iodide → 1-{4-[4-(3,4-Dichlorophenyl)piperazin-1-yl]butyl}-1,5,6,7-tetrahydroindol-4-one

HRID 1907832Notes

Reaction equation

HRID 1907832 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:15])[C:9]=2[CH:8]=[CH:7]1.[I-].[Na+].[Cl:18][C:19]1[CH:20]=[C:21]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:22]=[CH:23][C:24]=1[Cl:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.ClCCl.C(OCC)(=O)C.ClCCl>[Cl:18][C:19]1[CH:20]=[C:21]([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:14]4[CH2:13][CH2:12][CH2:11][C:10](=[O:15])[C:9]=4[CH:8]=[CH:7]3)[CH2:28][CH2:27]2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 936011-(3,4-Dichlorophenyl)piperazineHCID 235028891-(4-Chlorobutyl)-1,5,6,7-tetrahydroindol-4-one

Product 1

HCID 114300761-{4-[4-(3,4-Dichlorophenyl)piperazin-1-yl]butyl}-1,5,6,7-tetrahydroindol-4-oneYield 91.8%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A mixture of 1-(4-Chlorobutyl)-1,5,6,7-tetrahydroindol-4-one (600 mg) from step 1 and sodium iodide (438 mg) in acetonitrile (10 mL) was heated at reflux for 6 hours. (3,4-Dichlorophenyl)piperazine (581 mg) and potassium carbonate (367 mg) was then added and reflux continued for 16 h. TLC (ethyl acetate:dichloromethane 1:1) showed complete reaction. The reaction was poured into ice cold water (50 mL) and stirred for 0.5 hours. An oil separated out and was isolated from the mixture. The oil was dissolved with dichloromethane (15 mL), washed with water and brine, then dried with sodium sulfate, filtered and the solvent removed under vacuum to yield the title compound as an oil (970 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperaturereflux
  4. customreaction
  5. customAn oil separated out
  6. customwas isolated from the mixture
  7. washwashed with water and brine
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-ee8769be30a24368a10e93b35b79195f
Source dataset
uspto-grants-2013_12
Patent number
US08598180B2

Reaction notes

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