Ethanol → 8-Methoxy-8-(trifluoromethyl)-1,3-diazaspiro[4.5]decane-2,4-dione

HRID 922122Notes

Reaction equation

HRID 922122 reaction equation
[CH3:1][O:2][C:3]1([C:10]([F:13])([F:12])[F:11])[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[C-]#N.[Na+].[C:17](=[O:20])([O-])[O-].[NH4+:21].[NH4+:22].[CH2:23]([OH:25])C>O>[CH3:1][O:2][C:3]1([C:10]([F:13])([F:12])[F:11])[CH2:8][CH2:7][C:6]2([NH:22][C:23](=[O:25])[NH:21][C:17]2=[O:20])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 894014664-Methoxy-4-(trifluoromethyl)cyclohexan-1-one

Product 1

HCID 712474398-Methoxy-8-(trifluoromethyl)-1,3-diazaspiro[4.5]decane-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

8.80 g (44.86 mmol) of 4-methoxy-4-(trifluoromethyl)cyclohexanone (Example 11A), 4.40 g (89.72 mmol) of sodium cyanide and 17.24 g (179.44 mmol) of ammonium carbonate were suspended in 102 ml of ethanol and 102 ml of water. The resulting suspension was stirred at 60° C. for 20 hours. The precipitated product was filtered off, washed with water and dried under reduced pressure. This gave 10.05 g (84% of theory) of the title compound as a white powder.

Workup

  1. filtrationThe precipitated product was filtered off
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-47c7ceded0684042ac117066cd7f788c
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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