Diethyl Ether → HCID 19786544, compound

HRID 1646744Notes

Reaction equation

HRID 1646744 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH:6]1[C:21](=[O:22])[C:10]2[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])=[N:12][O:13][C:9]=2[CH2:8][CH2:7]1)[CH3:4].Cl.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37]CNC[CH2:33]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>O>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:11]1[C:10]2[C:21](=[O:22])[CH:6]([CH2:5][N:3]3[CH2:2][CH2:33][N:32]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[O:25][CH3:24])[CH2:37][CH2:4]3)[CH2:7][CH2:8][C:9]=2[O:13][N:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 19786590HCID 19786590, compound

Product 1

HCID 19786544HCID 19786544, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution consisting of 6,7-dihydro-5-dimethylaminomethyl-3-(2-fluorophenyl)-1,2-benzisoxazol-4(5H)-one hydrochloride (2.40 g) in distilled water (24 ml) was added 1-(2-methoxyphenyl)piperazine hydrochloride (3.38 g) and potassium carbonate (1.02 g) at room temperature with stirring. The resulting reaction mixture was heated to reflux for 25 min. and allowed to cool to room temperature. Diethyl ether was then added and the layers separated. The aqueous phase was extracted twice with ether. The combined organics were washed with brine and dried (Na2SO4). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, ether) afforded 2.45 g of 6,7-dihydro-3-(2-fluorophenyl)-5-(4-(2-methoxyphenyl)-1-piperazinyl)methyl-1,2-benzisoxazol-4(5H)-one as a foam. The compound was flushed thru alumina with dichloromethane to give an oil. The maleate was prepared in ethanol and the resulting salt was washed with ether, m.p. 153°-155°2C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 25 min.
  4. customthe layers separated
  5. extractionThe aqueous phase was extracted twice with ether
  6. washThe combined organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltration and concentration
  9. customgave the crude product
  10. customPurification via flash column chromatography (silica gel, ether)

Sources & evidence

ORD record
ord-ec5206fcbe2b4ceb88dfd8124ef658b0
Source dataset
uspto-grants-1993_01
Patent number
US05180834

Reaction notes

Loading…