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Potassium Carbonate → 4-(2-Chlorophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]piperazine hydrochloride

HRID 485489
Notes
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Reaction equation

HRID 485489 reaction equation
O.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl[CH2:17][CH2:18][CH2:19][C:20]1[C:24]2[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=2[O:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CN(C)C=O>[ClH:3].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:17][CH2:18][CH2:19][C:20]2[C:24]3[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=3[O:22][N:21]=2)[CH2:12][CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazoleHCID 202358491-(2-Chlorophenyl)piperazine hydrate hydrochloride

Product 1

HCID 135207354-(2-Chlorophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]piperazine hydrochlorideYield 139.6%

Reagents, catalysts & solvents 2

HCID 4875
Potassium Iodide
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To 40 ml of dimethylformamide was added, 5.0 g of 1-(2-chlorophenyl)piperazine hydrochloride hydrate, 6.4 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 10 g of milled potassium carbonate, and 0.01 g of potassium iodide, and the mixture was stirred at 90° C. for 2 hrs. The mixture was cooled, filtered and the filtrate evaporated to an oil. The oil was stirred with 100 ml water for five mins and then extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, the solution was acidified to pH 1 with ethereal hydrogen chloride, and the precipitate was collected and dried to give 5.7 g (70%) of product, mp 195° C. (dec). Two recrystallizations from ethyl acetate/methanol (5:1) gave the analytical sample, mp 228° C. (dec).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated to an oil
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water (2×), saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customthe precipitate was collected
  10. customdried

Sources & evidence

ORD record
ord-756cadf3417a441481da79d661ef0f01
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