Hydrochloric Acid → 7-[3-[4-(6-Fluorobenzo[d]isoxazole-3-yl)piperidin-1-yl]propoxy]-4-oxochromene-3-carboxylic acid hydrochloride

HRID 635222Notes

Reaction equation

HRID 635222 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:19])[C:11]([C:16]([OH:18])=[O:17])=[CH:12][O:13]2)=[CH:8][CH:7]=1.Cl.[F:21][C:22]1[CH:36]=[CH:35][C:25]2[C:26]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[N:27][O:28][C:24]=2[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>CN(C)C=O.O>[ClH:1].[F:21][C:22]1[CH:36]=[CH:35][C:25]2[C:26]([CH:29]3[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[CH:15]=[C:14]5[C:9]([C:10](=[O:19])[C:11]([C:16]([OH:18])=[O:17])=[CH:12][O:13]5)=[CH:8][CH:7]=4)[CH2:33][CH2:34]3)=[N:27][O:28][C:24]=2[CH:23]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 10636671HCID 10636671, compoundHCID 11334359R-56109 hydrochloride

Product 1

HCID 98922907-[3-[4-(6-Fluorobenzo[d]isoxazole-3-yl)piperidin-1-yl]propoxy]-4-oxochromene-3-carboxylic acid hydrochlorideYield 41.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.87 g (3 mmoles) of 7-(3-chloropropoxy)-4-oxochromene-3-carboxylic acid, 0.7 g (3 mmoles) of 6-fluoro-3-(4-piperidinyl)-benzo[d]isoxazole hydrochloride, 0.85 g (6 mmoles) of anhydrous potassium carbonate and a catalytic amount of potassium iodide in 25 mL of N,N-dimethylformamide was heated to 89-90° C. for 24 hours. After being cooled, the solution was poured onto 125 mL of water and then neutralized with HCl at pH 7. The precipitate obtained was filtered, washed with water and dried at vaccum. The solid was dissolved in 60 mL of 0.1M NaOH, diluted with water to 300 mL and the solution was washed with ethyl acetate. The aqueous solution was acidified with HCl to pH 1-2, and the precipitate obtained was filtered and dried at vaccum to give 0.62 g of 7-[3-[4-(6-fluorobenzo[d]isoxazole-3-yl)piperidin-1-yl]propoxy]-4-oxochromene-3-carboxylic acid hydrochloride in 40% yield.

Workup

  1. temperatureAfter being cooled
  2. customThe precipitate obtained
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried at vaccum
  6. dissolutionThe solid was dissolved in 60 mL of 0.1M NaOH
  7. additiondiluted with water to 300 mL
  8. washthe solution was washed with ethyl acetate
  9. customthe precipitate obtained
  10. filtrationwas filtered
  11. customdried at vaccum

Sources & evidence

ORD record
ord-b920cce5c9a443cd8d0d61d11bd1138c
Source dataset
uspto-grants-2001_02
Patent number
US06187793B1

Reaction notes

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