Cyanogen Bromide → HCID 13078343, compound

HRID 370906Notes

Reaction equation

HRID 370906 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:12]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=3[O:10][N:9]=2)[CH2:4][CH2:3]1.[N:18]#CBr.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[C:1]([N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:12]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=3[O:10][N:9]=2)[CH2:4][CH2:3]1)#[N:18]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 13076412HCID 13076412, compound

Product 1

HCID 13078343HCID 13078343, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 0.5 g of 3-(1-methyl-4-piperidyl)-5-methyl-1,2-benzisoxazole, 0.37 g of cyanogen bromide and 1.5 g of potassium carbonate in 50 ml of chloroform was heated under reflux for 48 hrs and stirred at room temperature for 48 hrs. The reaction was filtered, the solvent was removed and the residue was triturated with hexane to give a solid. The solid was recrystallized from hexane (three times) to give 0.178 g (37%) of product, mp, 125°-126°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hrs
  3. filtrationThe reaction was filtered
  4. customthe solvent was removed
  5. customthe residue was triturated with hexane
  6. customto give a solid
  7. customThe solid was recrystallized from hexane (three times)

Sources & evidence

ORD record
ord-367315d5e59046ef91b093df82002b33
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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