Sodium Hydroxide → HCID 18441739, compound

HRID 458156Notes

Reaction equation

HRID 458156 reaction equation
[C:1]1([N: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([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]2=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C[Si]([C:35]#[N:36])(C)C.[OH-].[Na+]>CC(O)=O>[O:17]=[C:10]1[C:11]2([CH2:12][CH2:13][N:14]([C:25]3([C:35]#[N:36])[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]3[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:15][CH2:16]2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][NH:9]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 82115Trimethylsilyl cyanideHCID 955922-Phenylcyclohexanone

Product 1

HCID 18441739HCID 18441739, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 0.26 g (1.15 mmol) 1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one in 2 ml AcOH were added 0.2 g (1.15 mmol) rac-2-phenylcyclohexanone followed by the dropwise addition of 0.86 ml (5.75 mmol) trimethylsilyl cyanide. The resulting mixture was heated to 80° C. overnight. The reaction mixture was poured onto 200 ml iced sodium hydroxide (25%,) and the resulting colorless solid filtered off. The solid was dissolved in 50 ml dichloromethane and washed with 40 ml water, dried over Na2SO4, filtered and evaporated: 52 mg 1-(4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-8-yl)-2-phenyl-cyclohexane-carbonitrile as colorless solid; MS (ISP): 415.4 MH+.

Workup

  1. filtrationthe resulting colorless solid filtered off
  2. dissolutionThe solid was dissolved in 50 ml dichloromethane
  3. washwashed with 40 ml water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e83899b0ea1444deae8771f57a31b909
Source dataset
uspto-grants-2007_03
Patent number
US07189850B2

Reaction notes

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