Cyanogen Bromide → HCID 20344019, compound

HRID 2049690Notes

Reaction equation

HRID 2049690 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1)#[N:2].[N:24]#CBr.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[C:9]([N:6]1[CH2:7][CH2:8][C:3]([C:1]#[N:2])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[CH2:4][CH2:5]1)#[N:24]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 20344006HCID 20344006, compound

Product 1

HCID 20344019HCID 20344019, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 19.8 g of 4-cyano-4-[2-(4-fluorophenylthio)phenyl]-1-methylpiperidine, Example 26(e), in 200 ml of chloroform is added portionwise over a 15 minute span to a mixture of 33.4 g of 97% cyanogen bromide and 130 g of potassium carbonate in 250 ml of chloroform. After total addition, the mixture is successively refluxed for 16 hours, cooled, filtered, washed thrice with 300 ml portions of water and one 50 ml portion of a saturated sodium chloride solution and dried. The resulting residue is dissolved in benzene, decolorized with charcoal and then filtered through celite. The solution's volume is reduced and rediluted with hexane to provide 1,4-dicyano-4-[2-(4-fluorophenylthio)phenyl]piperidine.

Workup

  1. additionAfter total addition
  2. temperaturethe mixture is successively refluxed for 16 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washwashed thrice with 300 ml portions of water and one 50 ml portion of a saturated sodium chloride solution
  6. customdried
  7. dissolutionThe resulting residue is dissolved in benzene
  8. filtrationfiltered through celite
  9. additionrediluted with hexane

Sources & evidence

ORD record
ord-62813cab338e43579e314d923f37e26c
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

Loading…