Ammonia → HCID 66817154, compound

HRID 1754897Notes

Reaction equation

HRID 1754897 reaction equation
[Cl-].[NH4+:2].[NH3:3].[Cl:4][C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1.[C-:21]#N.[Na+]>CN(C)C=O>[NH2:2][C:17]1([C:21]#[N:3])[CH2:18][CH2:19][N:14]([S:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([Cl:4])[CH:6]=2)(=[O:13])=[O:12])[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 21519187HCID 21519187, compound

Product 1

HCID 66817154HCID 66817154, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ammonium chloride (790 mg, 14.77 mmol) and a 28% aqueous ammonia solution (2.2 mL) were added to a solution of 1-(3-chloro-benzenesulfonyl)-piperidin-4-one (3.11 g, 11.36 mmol) in dimethylformamide (15 mL), and the mixture was stirred at room temperature for one hour. Thereafter, sodium cyanide (724 mg, 14.77 mmol) was added, and the mixture was further stirred for 17 hours and then quenched with a saturated aqueous sodium carbonate solution. The organic layer and the aqueous layer were separated, and the aqueous layer was then further extracted with ethyl acetate:n-hexane (4:1). The organic layers were combined, washed with water (×4), and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:3) to give 4-amino-1-(3-chloro-benzenesulfonyl)-piperidine-4-carbonitrile as a white solid (2.41 g, 71%).

Workup

  1. stirringthe mixture was further stirred for 17 hours
  2. customquenched with a saturated aqueous sodium carbonate solution
  3. customThe organic layer and the aqueous layer were separated
  4. extractionthe aqueous layer was then further extracted with ethyl acetate:n-hexane (4:1)
  5. washwashed with water (×4)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-b0b8e823dc9a4325b3210718810bc7f2
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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