Sulfuric Acid → 8-Benzyl-2,8-diazaspiro[4.5]decane-1,3-dione

HRID 491471Notes

Reaction equation

HRID 491471 reaction equation
S(=O)(=O)(O)[OH:2].[CH2:6]([N:13]1[CH2:18][CH2:17][C:16]([CH2:21][C:22]#[N:23])([C:19]#N)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-:24].[Na+]>C(O)(=O)C>[CH2:6]([N:13]1[CH2:14][CH2:15][C:16]2([C:19](=[O:24])[NH:23][C:22](=[O:2])[CH2:21]2)[CH2:17][CH2:18]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 128476541-Benzyl-4-(cyanomethyl)piperidine-4-carbonitrile

Product 1

HCID 221109398-Benzyl-2,8-diazaspiro[4.5]decane-1,3-dioneYield 81.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (56.8 ml) and sulfuric acid (11.8 ml) are added to 1-benzyl-4-cyanomethyl-piperidine-4-carbonitrile (27.2 g, 0.114 mmol) at ambient temperature. The reaction mixture is stirred at 125 C.° for 1 h, cooled down to the room temperature and added to saturated NaOH aq. to adjust to pH 6.0. The mixture is extracted with dichloromethane. The combined extracts are washed with H2O and brine, dried over sodium sulfate and evaporated down to give 8-benzyl-2,8-diaza-spiro[4.5]decane-1,3-dione (three steps yield: 81.8%).

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washThe combined extracts are washed with H2O and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated down

Sources & evidence

ORD record
ord-bc0498391352468eb616c3b1656b6b4d
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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