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Potassium Iodide → 7-[3-[4-(6-Fluorobenzo[d]isoxazole-3-yl)piperidin-1-yl]propoxy]-2-(hydroxymethyl)-chromen-4-one

HRID 635225
Notes
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Reaction equation

HRID 635225 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:18])[CH:11]=[C:12]([CH2:16][OH:17])[O:13]2)=[CH:8][CH:7]=1.Cl.[F:20][C:21]1[CH:35]=[CH:34][C:24]2[C:25]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:26][O:27][C:23]=2[CH:22]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>C(#N)C.C(OCC)C.O>[F:20][C:21]1[CH:35]=[CH:34][C:24]2[C:25]([CH:28]3[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[CH:15]=[C:14]5[C:9]([C:10](=[O:18])[CH:11]=[C:12]([CH2:16][OH:17])[O:13]5)=[CH:8][CH:7]=4)[CH2:32][CH2:33]3)=[N:26][O:27][C:23]=2[CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 105398897-(3-Chloropropoxy)-2-(hydroxymethyl)-chromen-4-oneHCID 11334359R-56109 hydrochloride

Product 1

HCID 98268277-[3-[4-(6-Fluorobenzo[d]isoxazole-3-yl)piperidin-1-yl]propoxy]-2-(hydroxymethyl)-chromen-4-oneYield 40.2%

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3 g (11 mmoles) of the compound obtained in Example 5, 2.88 g (11 mmoles) of 6-fluoro-3-(4-piperidinyl)-benzo[d]isoxazole hydrochloride, 2.16 g (26 mmoles) of sodium bicarbonate and a catalytic amount of potassium iodide in 80 mL of acetonitrile was heated at reflux for 48 hours. The mixture was then allowed to cool, poured onto 100 mL of water and extracted with 100 mL of chloroform. The chloroform extract was washed with water, dried over sodium sulphate and evaporated. The residue obtained was suspended in ethyl ether, filtered and dried at vaccum to give 2 g of 7-[3-[4-(6-fluorobenzo[d]isoxazole-3-yl)piperidin-1-yl]propoxy]-2-(hydroxymethyl)-chromen-4-one in 40% yield.

Workup

  1. temperatureat reflux for 48 hours
  2. temperatureto cool
  3. extractionextracted with 100 mL of chloroform
  4. extractionThe chloroform extract
  5. washwas washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe residue obtained
  9. filtrationfiltered
  10. customdried at vaccum

Sources & evidence

ORD record
ord-f9b3726068ce46738c1869d3260eaa2d
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06187793B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes