Cyclohexanone → Rac-1-(1-oxo-4-phenyl-2,8-diaza-spiro [4.5]dec-8-yl)-cyclohexanecarbonitrile

HRID 914935Notes

Reaction equation

HRID 914935 reaction equation
[C:1]1([CH:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Si]([C:29]#[N:30])(C)(C)C>CC(O)=O>[O:17]=[C:10]1[C:11]2([CH2:12][CH2:13][N:14]([C:18]3([C:29]#[N:30])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:15][CH2:16]2)[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][NH:9]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 82115Trimethylsilyl cyanideHCID 127097244-Phenyl-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 69486548Rac-1-(1-oxo-4-phenyl-2,8-diaza-spiro [4.5]dec-8-yl)-cyclohexanecarbonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of rac-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one (8.0 g, 34.7 mmol) in AcOH (80 mL) was added cyclohexanone (3-4 g, 34.7 mmol) followed by the dropwise addition of TMSCN (10.4 g, 104.2 mmol) and the resulting mixture stirred at room temperature for 5 days. The resulting mixture was poured onto ice—sodium hydroxide (25%, 200 mL) and the resulting white solid filtered off. The solid was dissolved in DCM (50 mL) and washed with water (40 mL) and dried over sodium sulfate. Filtration and evaporation afforded the title compound (7.25 g, 62%) as a white solid after purification by silica gel chromatography eluting with DCM: MeOH (9: 1). MS: m/e=338.3 (M+H).

Workup

  1. additionThe resulting mixture was poured onto ice—sodium hydroxide (25%, 200 mL)
  2. filtrationthe resulting white solid filtered off
  3. dissolutionThe solid was dissolved in DCM (50 mL)
  4. washwashed with water (40 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-ebe38b8c6a0445c7a9642891ee908571
Source dataset
uspto-grants-2007_09
Patent number
US07265126B2

Reaction notes

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