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Potassium Iodide → 5-Fluoro-3-(1-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}piperidin-4-ylmethyl)-1H-indole

HRID 1108210
Notes
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Reaction equation

HRID 1108210 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[I-].[K+].[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.Cl[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:41][CH3:42])[CH2:31][CH2:30]1>C(#N)C.O>[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:1][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][N:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])[CH2:31][CH2:30]2)[CH2:22][CH2:21]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazineHCID 112877165-fluoro-3-[(4-piperidinyl)methyl]-1H-indole

Product 1

HCID 98257145-Fluoro-3-(1-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}piperidin-4-ylmethyl)-1H-indoleYield 76%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Pulverized potassium carbonate (0.33 g, 2.4 mmole) and potassium iodide (0.40 g, 2.4 mmole) was added to a mixture of 4-(5-fluoro-1H-indol-3-yl)methylpiperidine (0.5 g, 2.3 mmole) and 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine (0.58 g, 2.3 mmole) in 20 ml of acetonitrile. The resulting mixture was heated to reflux under nitrogen for 3 hours. After cooling, it was diluted with water (150 ml) and the product extracted into ethyl acetate (50 ml). The organic layer was washed with water (50 ml), brine (50 ml), and after drying over sodium sulfate, filtration and concentration in vacuo afforded the required product as a white solid (0.78 g, 76%). Treatment with an excess of 0.25M ethanolic fumaric acid solution gave the acid addition salt, which was recrystallized from ethanol/diethyl ether to afford the title product as white needles.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux under nitrogen for 3 hours
  3. temperatureAfter cooling
  4. extractionthe product extracted into ethyl acetate (50 ml)
  5. washThe organic layer was washed with water (50 ml), brine (50 ml)
  6. dry with materialafter drying over sodium sulfate, filtration and concentration in vacuo

Sources & evidence

ORD record
ord-5e0f2841f09c4f7ea002ca9e5f0ee84c
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06066637

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes