Potassium Cyanide → HCID 66818447, compound

HRID 1755110Notes

Reaction equation

[C-:1]#[N:2].[K+].C([O-])(=O)C.[NH4+:8].[CH2:9]([O:12][CH2:13][CH2:14][N:15]([CH3:37])[C:16](=[O:36])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][S:25]([N:28]2[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)(=[O:27])=[O:26])=[C:19]([CH3:35])[CH:18]=1)[CH:10]=[CH2:11].C(=O)(O)[O-].[Na+]>CO>[CH2:9]([O:12][CH2:13][CH2:14][N:15]([CH3:37])[C:16](=[O:36])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][S:25]([N:28]2[CH2:33][CH2:32][C:31]([NH2:8])([C:1]#[N:2])[CH2:30][CH2:29]2)(=[O:26])=[O:27])=[C:19]([CH3:35])[CH:18]=1)[CH:10]=[CH2:11]

Participants

Conditions

Temperature: 65 °C

Procedure

Potassium cyanide (382 mg, 5.87 mmol) and ammonium acetate (513 mg, 6.65 mmol) were added to a solution of N-(2-allyloxy-ethyl)-3,N-dimethyl-4-[2-(4-oxo-piperidine-1-sulfonyl)-ethyl]-benzamide (1.65 g, 3.91 mmol) in methanol (20 ml), and the mixture was stirred at 65° C. for three hours. Sodium bicarbonate (290 mg) was added to the reaction solution, and the mixture was then concentrated under reduced pressure. Water was added to the resulting residue, followed by extraction with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give N-(2-allyloxy-ethyl)-4-[2-(4-amino-4-cyano-piperidine-1-sulfonyl)-ethyl]-3,N-dimethyl-benzamide (1.57 g) as a crude compound.

Workup

concentrationthe mixture was then concentrated under reduced pressure
additionWater was added to the resulting residue
extractionfollowed by extraction with methylene chloride
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-257ba97ad9ec4466b65da831f9dc175b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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