Potassium Cyanide → HCID 66817117, compound

HRID 1755052Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[C-:6]#[N:7].[K+].[CH3:9][C:10]1[CH:15]=[C:14]([NH:16][CH3:17])[CH:13]=[C:12]([CH3:18])[C:11]=1/[CH:19]=[CH:20]/[S:21]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)(=[O:23])=[O:22].C([O-])(O)=O.[Na+]>CO>[NH2:5][C:27]1([C:6]#[N:7])[CH2:28][CH2:29][N:24]([S:21](/[CH:20]=[CH:19]/[C:11]2[C:10]([CH3:9])=[CH:15][C:14]([NH:16][CH3:17])=[CH:13][C:12]=2[CH3:18])(=[O:23])=[O:22])[CH2:25][CH2:26]1

Participants

Conditions

Temperature: 60 °C

Procedure

Ammonium acetate (686 mg, 8.91 mmol) and potassium cyanide (541 mg, 8.31 mmol) were added to a solution of 1-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-piperidin-4-one (1.91 g, 5.94 mmol) in MeOH (20 ml), and the mixture was heated with stirring at 60° C. for three hours. The mixed reaction solution was cooled and a saturated aqueous NaHCO3 solution was then added, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was triturated with hexane:CH2Cl2=7:3 to give 4-amino-1-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-piperidine-4-carbonitrile (1.86 g, 89%).

Workup

temperaturethe mixture was heated
customThe mixed reaction solution
temperaturewas cooled
extractionfollowed by extraction with ethyl acetate
washThe organic layer was sequentially washed with water and saturated brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe resulting residue was triturated with hexane

Sources & evidence

ORD record: ord-0d6aebfef4ec4fff8ebedcbdbeecf980
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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