Potassium Carbonate → HCID 21960019, compound

HRID 744327Notes

Reaction equation

HRID 744327 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.Br[CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][C:24]=1[O:32][CH3:33].C([O-])([O-])=O.[K+].[K+].[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]/[C:43]([OH:45])=[O:44]>C(O)C.C(#N)C>[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]/[C:43]([OH:45])=[O:44].[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]4[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][C:24]=4[O:32][CH3:33])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 444972Fumaric AcidHCID 13076430HCID 13076430, compoundHCID 144071711-[4-(4-Bromobutoxy)3-methoxyphenyl]ethanone

Product 1

HCID 21960019HCID 21960019, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 6-chloro-3-(4-piperidinyl)-1,2-benzisoxazole (4.7 g, 20 mmol), 1-[4-(4-bromobutoxy)-3-methoxyphenyl]ethanone (6.0 g, 20 mmol), K2CO3 (2.8 g) and acetonitrile (120 ml) was refluxed for 16 hours. The reaction was allowed to cool, filtered, and the filtrate was concentrated to 9.9 g of a brown oil. The oil was chromatographed on a Waters Prep 500 utilizing silica gel columns and eluting with methylene chloride/methanol (5%). Concentration of the appropriate fractions afforded 2:3 g of an off-white solid. The solid was dissolved in ethanol and fumaric acid (0.62 g, 1.1 eq.) was added. Upon concentration of the ethanol, a crude, brown solid was collected, which was taken up in refluxing acetone. Upon cooling, a white solid crystallized from solution yielding 2.2 g (19%) of 1-[4-[4-[4-(6-chloro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-butoxy]-3-methoxyphenyl]ethanone fumarate as a white solid, m.p.=139°-141° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to 9.9 g of a brown oil
  5. customThe oil was chromatographed on a Waters Prep 500 utilizing silica gel columns
  6. washeluting with methylene chloride/methanol (5%)
  7. customConcentration of the appropriate fractions afforded 2
  8. customUpon concentration of the ethanol, a crude, brown solid was collected
  9. temperaturein refluxing acetone
  10. temperatureUpon cooling
  11. customa white solid crystallized from solution

Sources & evidence

ORD record
ord-2889a049af6d448b87272e14c604f5c8
Source dataset
uspto-grants-1996_09
Patent number
US05559117

Reaction notes

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