Potassium Iodide → HCID 13076447, compound

HRID 2417721Notes

Reaction equation

HRID 2417721 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:3][CH2:2]1.[CH2:17](Br)[CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl-:29].[Na+]>CN(C)C=O.O.C(O)C>[ClH:29].[CH2:19]([N:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:5][CH2:6]1)[CH:18]=[CH2:17]

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 5234Sodium Chloride2×HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 13076447HCID 13076447, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4.95 g of 3-(4-piperidyl)-6-fluoro-1,2-benzisoxazole, 3.0 g of allyl bromide, 3.0 g of potassium carbonate and some crystals of potassium iodide in 70 ml of dimethylformamide was stirred under nitrogen at 85°-90° for 5 hrs. The reaction was cooled and added to 40 ml ethanol. Half-saturated sodium chloride, prepared by adding an equal volume of water to saturated sodium chloride solution was added. After 16 hrs, the crystals were filtered, washed with water and dried, yielding 3.4 g of base. The base was dissolved in 60 ml of ethanol and 1.5 ml conc hydrochloric acid. The mixture was heated to 50° and the solvents were evaporated in vacuo. Benzene (60 ml) was added and distilled off in vacuo, yielding a residue. The residue was triturated with ether, filtered and twice recrystallized from isopropanol-ether to give 2.4 g (59.3%) of product, mp, 198°.

Workup

  1. temperatureThe reaction was cooled
  2. additionwas added
  3. filtrationthe crystals were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-efa6f23c861640ab81f7f99415c01b79
Source dataset
uspto-grants-1984_09
Patent number
US04469869

Reaction notes

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