Cyanogen Bromide → HCID 20343953, compound

HRID 2049872Notes

Reaction equation

HRID 2049872 reaction equation
[CH2:1]([C:3]([C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1)=[O:4])[CH3:2].C(O)(=O)C(O)=O.C(C(C1(C2C=CC=CC=2SC2C=CC=CC=2)CC[N:38](C)CC1)=O)C.C(=O)([O-])[O-].[K+].[K+].N#CBr>C(Cl)(Cl)Cl.C(O)C>[C:11]([N:8]1[CH2:7][CH2:6][C:5]([C:3]([CH2:1][CH3:2])=[O:4])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)#[N:38]

Participants

7

Reactant 4

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 20343978HCID 20343978, compoundHCID 20343979HCID 20343979, compound

Product 1

HCID 20343953HCID 20343953, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 3.2 g of 4-ethylcarbonyl-1-methyl-4-(2-phenylthiophenyl)piperidine, free base of Example 5 in 300 ml of chloroform is added portionwise over a 10 minute span to a refluxing mixture of 7.5 g of potassium carbonate and 2.0 g of cyanogen bromide in 30 ml of chloroform. After total addition, stirring is continued at reflux for two additional hours. Thereafter, the mixture is filtered and the filtrate is concentrated to dryness, leaving an oil residue. The residue is taken up in about 50 ml of ethyl alcohol and the alcoholic solution is heated on a steam bath for 5-10 minutes before evaporating off the solvent. The resulting oil solidifies on standing and the solid is recrystallized from a benzene-hexane mixture to provide 1-cyano-4-ethylcarbonyl-4-(2-phenylthiophenyl)-piperidine.

Workup

  1. additionAfter total addition
  2. temperatureat reflux for two additional hours
  3. filtrationThereafter, the mixture is filtered
  4. concentrationthe filtrate is concentrated to dryness
  5. customleaving an oil residue
  6. temperaturethe alcoholic solution is heated on a steam bath for 5-10 minutes
  7. custombefore evaporating off the solvent
  8. customthe solid is recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-aff2da5b48ce4099a26e20a5df5efeb4
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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