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Potassium Iodide → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-n-butylpiperazine dihydrochloride

HRID 485496
Notes
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Reaction equation

HRID 485496 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.[ClH:15].Cl.[CH2:17]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:1].[ClH:15].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:24]3[CH2:25][CH2:26][N:21]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23]3)=[N:6][O:7][C:8]=2[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazoleHCID 225914051-n-Butylpiperazine dihydrochloride

Product 1

HCID 135207531-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-n-butylpiperazine dihydrochlorideYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 12 g of 3-(-chloropropyl)-6-fluoro-1,2-benzisoxazole, 10 g of 1-n-butylpiperazine dihydrochloride, 21 g of potassium carbonate and a few crystals of potassium iodide in 80 ml of dimethylformamide was stirred at 70° C. for three hrs, cooled, filtered and concentrated to an oil. The oil was stirred with water and extracted with ether. The ether extracts were washed with water, saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was converted to a salt by treatment with ethereal hydrogen chloride. Recrystallization from ethyl acetate/methanol gave 3.2 g (18%) of product, mp 260° C. (dec).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated to an oil
  4. extractionextracted with ether
  5. washThe ether extracts were washed with water, saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customRecrystallization from ethyl acetate/methanol

Sources & evidence

ORD record
ord-f164a75553f544798a4014d4fc18c696
Source dataset
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04536578

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes