Ammonia → HCID 57034239, compound

HRID 397659Notes

Reaction equation

HRID 397659 reaction equation
[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([O:19]C)=O)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:21]>O1CCOCC1>[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([NH2:21])=[O:19])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57106621HCID 57106621, compound

Product 1

HCID 57034239HCID 57034239, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl (2S)-1-[(cyclohexylmethyl)sulfonyl]-2-piperidinecarboxylate (3.0 g) [see Preparation 25) was dissolved in 1,4-dioxane (30 ml) and 0.88 aqueous ammonia solution (25 ml) was added. Ammonia gas was bubbled through the mixture for 20 mins. and the reaction mixture was heated to 100° C. in a sealed vessel for 56 hours. After this time the mixture was cooled and the solvent removed under reduced pressure. The residue was taken up in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate solution, brine, dried over magnesium sulphate and the solvent was removed under reduced pressure to afford (2S)-1-[(cyclohexylmethyl)sulfonyl]-2-piperidinecarboxamide (1.77 g) as a colourless oil.

Workup

  1. customPreparation 25)
  2. customAmmonia gas was bubbled through the mixture for 20 mins
  3. temperatureAfter this time the mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution, brine
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-975e4825c12541e9bdd779e43d96f90c
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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