Acetone Cyanohydrin → HCID 59863012, compound

HRID 2064071Notes

Reaction equation

HRID 2064071 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[C:13]([O:16][C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:21])[CH2:3][CH2:2]1.O[C:23]([CH3:27])([CH3:26])[C:24]#[N:25].[O:28]1[CH2:33]CC(=O)C[CH2:29]1>CN(C)C(=O)C>[O:21]=[C:8]1[N:7]([CH:4]2[CH2:5][CH2:6][N:1]([C:23]3([C:24]#[N:25])[CH2:27][CH2:33][O:28][CH2:29][CH2:26]3)[CH2:2][CH2:3]2)[C:11]2[CH:12]=[C:13]([O:16][C:17]([F:18])([F:20])[F:19])[CH:14]=[CH:15][C:10]=2[NH:9]1

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 121599Tetrahydro-4H-pyran-4-oneHCID 57423927HCID 57423927, compound

Product 1

HCID 59863012HCID 59863012, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-piperidin-4-yl-6-(trifluoromethoxy)-1,3-dihydro-2H-benzimidazol-2-one (D32, 301 mg), 2-hydroxy-2-methylpropanenitrile, (160 mg), tetrahydro-4H-pyran-4-one (200 mg) magnesium sulphate (600 mg) and N,N-dimethylacetamide (1 ml) were stirred at 60° C. under a slow stream of argon overnight. The resulting white paste was partitioned between dichloromethane and water and sonicated. The dichloromethane layer was separated, dried by passing through a 3 g hydromatrix cartridge. (Large proportion of the material was lost due to spillage). The solvent was removed and the title compound was obtained as a white solid from ether. Yield 62 mg. M+ 411.

Workup

  1. customThe resulting white paste was partitioned between dichloromethane and water
  2. customsonicated
  3. customThe dichloromethane layer was separated
  4. customdried
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-8b8939fc3c3f4bfc9707eafb4a4e4676
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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