Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | HCID 66817735 | HCID 66817735 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 66817117 | HCID 66817117 | 89.9% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09169254B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-0d6aebfef4ec4fff8ebedcbdbeecf980 |
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| Source note | uspto-grants-2015_10 |
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