Cyanogen Bromide → HCID 20343954, compound

HRID 2049881Notes

Reaction equation

HRID 2049881 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:22]#[N:23])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[N:30]#CBr>C(Cl)(Cl)Cl>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([S:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:5]2([C:22]#[N:23])[CH2:6][CH2:7][N:2]([C:1]#[N:30])[CH2:3][CH2:4]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 20343952HCID 20343952, compound

Product 1

HCID 20343954HCID 20343954, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 14.9 g of 1-methyl-4-cyano-4-[2-(4-chlorophenylthio)phenyl]piperidine, Example 1, in 75 ml of chloroform is added dropwise to a rapidly stirring mixture of 30.4 g of potassium carbonate and 7.6 g of cyanogen bromide in 80 ml of chloroform. After total addition, the reaction mixture is refluxed for 16 hours and then successively, filtered, washed thrice with 150 ml portions of water, washed once with 50 ml saturated sodium chloride solution and dried. The residue is dissolved in chloroform and the chloroform solution is chromatographed (silica gel F60, ether as eluant). The purified material is recrystallized from acetone to give 4-[2-(4-chlorophenylthio)phenyl]-1,4-dicyanopiperidine.

Workup

  1. additionAfter total addition
  2. temperaturethe reaction mixture is refluxed for 16 hours
  3. filtrationsuccessively, filtered
  4. washwashed thrice with 150 ml portions of water
  5. washwashed once with 50 ml saturated sodium chloride solution
  6. customdried
  7. dissolutionThe residue is dissolved in chloroform
  8. customthe chloroform solution is chromatographed (silica gel F60, ether as eluant)
  9. customThe purified material is recrystallized from acetone

Sources & evidence

ORD record
ord-df7ae9456b8b4dc0b995a390eed6692e
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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