Cyanogen Bromide → HCID 20343966, compound

HRID 2049870Notes

Reaction equation

HRID 2049870 reaction equation
C(O)(=O)C(O)=O.[C:7]([C:10]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)(=[O:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+].[N:36]#CBr>C(Cl)(Cl)Cl>[C:7]([C:10]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:15][CH2:14][N:13]([C:16]#[N:36])[CH2:12][CH2:11]1)(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 20344024HCID 20344024, compound

Product 1

HCID 20343966HCID 20343966, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 6.8 g of 4-acetyl-1-methyl-4-(2-phenylthiophenyl)piperidine oxalate, Example 6, in 40 ml of chloroform is added dropwise to a rapidly stirring mixture of 14.7 g of potassium carbonate and 3.7 g of cyanogen bromide in 48.5 ml of chloroform. After total addition, the reaction mixture is successively stirred at reflux for 16 hours, filtered, washed five times with 100 ml portions of water, washed with one 50 ml portion of a saturated sodium chloride solution and dried. The resulting product is purified by chromatography (silica gel column, ether eluant) to provide 4-acetyl-1-cyano-4-(2-phenylthiophenyl)piperidine.

Workup

  1. additionAfter total addition
  2. stirringthe reaction mixture is successively stirred
  3. temperatureat reflux for 16 hours
  4. filtrationfiltered
  5. washwashed five times with 100 ml portions of water
  6. washwashed with one 50 ml portion of a saturated sodium chloride solution
  7. customdried
  8. customThe resulting product is purified by chromatography (silica gel column, ether eluant)

Sources & evidence

ORD record
ord-5d01239edcf14a21952237590e089909
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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