Potassium Carbonate → HCID 178451986, compound

HRID 1507500Notes

Reaction equation

HRID 1507500 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)#[N:11]>O.C(O)C>[OH:3][NH:2][C:10]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[NH:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylate

Product 1

HCID 178451986HCID 178451986, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Into a mixture of hydroxylamine hydrochloride (52 g, 748.30 mmol, 3.00 equiv) and potassium carbonate (55.5 g, 402.47 mmol, 1.60 equiv) in water (125 mL) was added a solution of tert-butyl 4-cyanopiperidine-1-carboxylate (52.5 g, 249.68 mmol, 1.00 equiv) in ethyl alcohol (625 mL) dropwise with stirring. The resulting mixture was stirred overnight at 90° C. in an oil bath, cooled down to room temperature, filtered and concentrated under reducing pressure. The residue was diluted with 2000 mL of ethyl acetate, washed with 1×800 mL of water and dried over anhydrous sodium sulfate. Filtration and concentration under reducing pressure gave 60 g of tert-butyl 4-(N-hydroxycarbamimidoyl)piperidine-1-carboxylate as a white solid, which was used directly for next step without further purification. MS m/z [M+H]+ (ESI): 245.

Workup

  1. stirringThe resulting mixture was stirred overnight at 90° C. in an oil bath
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionThe residue was diluted with 2000 mL of ethyl acetate
  5. washwashed with 1×800 mL of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-d2cdf2cde38f42ce8ea43b82bb4c0859
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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