Potassium Carbonate → 6-Chloro-3{1-[4,4-bis(4-fluorophenyl)-1-butyl]-4-piperidyl}-1,2-benzisoxazole hydrochloride

HRID 223253Notes

Reaction equation

HRID 223253 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.Cl[CH2:18][CH2:19][CH2:20][CH:21]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:1].[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][CH:21]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 13076430HCID 13076430, compound

Product 1

HCID 130783756-Chloro-3{1-[4,4-bis(4-fluorophenyl)-1-butyl]-4-piperidyl}-1,2-benzisoxazole hydrochlorideYield 62.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 16.5 g of 6-chloro-3-(4-piperidyl)-1,2-benzisoxazole, 22.4 g of 4-chloro-1,1-bis(4-fluorophenyl)butane, 22.0 g of potassium carbonate and 200 ml of dimethylformamide was stirred and heated at 75° for 5 hrs. The reaction mixture was allowed to cool and was filtered. The filtrate was concentrated in vacuo to an oil, which was taken up in 300 ml ether and washed with an equal portion of brine. The ether layer was dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. The oil was dissolved in 65 ml of ethanol, the solution was cooled, and 20 ml of ether saturated with hydrogen chloride was added dropwise. Ether (400 ml) was added causing turbidity. The mixture was seeded and then stirred for 1/2 hour to produce the salt. Recrystallization from 800 l of 3:5 ethanol-ether gave 11.3 g (13% yield) of product, mp 205°-207°.

Workup

  1. temperatureheated at 75° for 5 hrs
  2. temperatureto cool
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated in vacuo to an oil, which
  5. washwashed with an equal portion of brine
  6. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo to an oil
  8. dissolutionThe oil was dissolved in 65 ml of ethanol
  9. temperaturethe solution was cooled
  10. addition20 ml of ether saturated with hydrogen chloride was added dropwise
  11. additionEther (400 ml) was added
  12. stirringstirred for 1/2 hour
  13. customto produce the salt
  14. customRecrystallization from 800 l of 3:5 ethanol-ether

Sources & evidence

ORD record
ord-ecb64508315143698f68b0fd0fdbad8c
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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