Potassium Carbonate → HCID 131722719, compound

HRID 1069301Notes

Reaction equation

HRID 1069301 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[CH:11]2.[F:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:21][O:22][C:18]=2[CH:17]=1.C([O-])([O-])=O.[K+].[K+].[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41]>C(OCC)(=O)C.O.C(#N)C>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41].[F:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([CH:23]3[CH2:24][CH2:25][N:26]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[CH:7]=[CH:8][CH:9]=[C:10]5[C:14]=4[NH:13][CH:12]=[CH:11]5)[CH2:27][CH2:28]3)=[N:21][O:22][C:18]=2[CH:17]=1.[F:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([CH:23]3[CH2:24][CH2:25][N:26]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[CH:7]=[CH:8][CH:9]=[C:10]5[C:14]=4[NH:13][CH:12]=[CH:11]5)[CH2:27][CH2:28]3)=[N:21][O:22][C:18]=2[CH:17]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 444972Fumaric AcidHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 153849647-(3-chloropropoxy)-1H-indole

Product 1

HCID 131722719HCID 131722719, compoundYield 54.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 7-(3-chloropropoxy)-1H-indole (3.5 g, 17 mmol), 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.5 g, 17 mmol), K2CO3 (2.3 g) and acetonitrile (60 ml) was refluxed for 11 hour The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed with water, dried (MgSO4), and the solvent was concentrated to afford a dark oil. The oil was flash chromatographed on silica gel. Upon concentration of the appropriate fractions, 3.0 g of a white, foamy substance was obtained. The substance was dissolved in ethyl acetate (75 ml) and fumaric acid (0.97 g, 83 mmol) was added. The mixture was briefly heated to reflux, and then stirred at ambient temperature for 1.5 hours. The resultant insoluble white fumarate salt was collected and afforded 4.2 g of product. Recrystallization of the salt from dimethylformamide yielded 3.1 g (36%) of 6-fluoro-3-[1-[3-1(1H-indol-7-yl)oxy]propyl]-4-piperidinyl]-1,2-benzisoxazole hemifumarate as a white solid, m.p.=213-215° C.

Workup

  1. temperaturewas refluxed for 11 hour The reaction
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. washThe ethyl acetate was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationthe solvent was concentrated
  6. customto afford a dark oil
  7. customchromatographed on silica gel
  8. customUpon concentration of the appropriate fractions, 3.0 g of a white, foamy substance was obtained
  9. temperatureThe mixture was briefly heated
  10. temperatureto reflux
  11. customThe resultant insoluble white fumarate salt was collected

Sources & evidence

ORD record
ord-6091c200acde40c49949177e95f71188
Source dataset
uspto-grants-2001_06
Patent number
US06251907B1

Reaction notes

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