Potassium Iodide → 6-Fluoro-3-(1-cyanomethyl-4-piperidyl)-1,2-benzisoxazole

HRID 223579

Reaction equation

HRID 223579 reaction equation
Cl.[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:27][C:28]#[N:29]>O.CN(C)C=O>[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:27][C:28]#[N:29])[CH2:14][CH2:15]3)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 11334359R-56109 hydrochloride

Product 1

HCID 130783426-Fluoro-3-(1-cyanomethyl-4-piperidyl)-1,2-benzisoxazoleYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.1 g of 6-fluoro-3-(4-piperidyl)-1,2-benzisoxazole hydrochloride, 4.9 g of potassium carbonate and 30 ml of dimethylformamide was stirred at ambient temperature for 5 min. Potassium iodide (0.24 g) was added, followed by 0.76 ml of chloroacetonitrile. The mixture was stirred and heated under nitrogen at 80°-85° for 2 hrs and then poured into 300 ml of water. The solid was collected and dried (vacuum oven). Recrystallization from ethanol-water yielded 2.0 g (64%) of product. An analytical sample was obtained by combining the 2.0 g sample with 0.8 g of another sample and recrystallizing from ethanol-water to give 2.2 g of product, mp, 126°-128°.

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated under nitrogen at 80°-85° for 2 hrs
  3. customThe solid was collected
  4. customdried (vacuum oven)
  5. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-85f8a657998849fc88e4ba7cb986e63a
Source dataset
uspto-grants-1982_10
Patent number
US04355037

Linked notes

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