Ethyl Acetate → HCID 19832524, compound

HRID 2051582Notes

Reaction equation

HRID 2051582 reaction equation
[CH:1]1([O:7][N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH:11]([OH:16])[CH2:10][C:9]2([CH3:18])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:21][N:22]([C:39]1[N:44]=[C:43](Cl)[N:42]=[C:41](Cl)[N:40]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:38])[C:30]1[N:35]=[C:34](Cl)[N:33]=[C:32](Cl)[N:31]=1.C([O:50][CH2:51][CH3:52])(=O)C>O1CCOCC1>[CH3:21][N:22]([C:39]1[N:44]=[C:43]([O:16][CH:11]2[CH2:10][C:9]([CH3:18])([CH3:17])[N:8]([O:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:13]([CH3:14])([CH3:15])[CH2:12]2)[N:42]=[C:41]([O:16][CH:11]2[CH2:10][C:9]([CH3:18])([CH3:17])[N:8]([O:50][CH:51]3[CH2:52][CH2:3][CH2:2][CH2:1][CH2:6]3)[C:13]([CH3:14])([CH3:15])[CH2:12]2)[N:40]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:38])[C:30]1[N:35]=[C:34]([O:16][CH:11]2[CH2:10][C:9]([CH3:18])([CH3:17])[N:8]([O:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:13]([CH3:14])([CH3:15])[CH2:12]2)[N:33]=[C:32]([O:16][CH:11]2[CH2:10][C:9]([CH3:18])([CH3:17])[N:8]([O:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:13]([CH3:14])([CH3:15])[CH2:12]2)[N:31]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-olHCID 19832520HCID 19832520, compound

Product 1

HCID 19832524HCID 19832524, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 22.6 g (88.6 mmol) of 1-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine, 2.13 g (88.6 mmol) of sodium hydride, and 150 ml of 1,4-dioxane is heated at reflux for 2.5 hours. The reaction mixture is cooled to 60° C. and treated with a solution of 7.8 g (17.7 mmol) of N,N'-dimethyl-N,N'-bis(2,4-dichloro-1,3,5-triazin-6-yl)-1,6-hexanediamine in 50 ml of dioxane. The reaction mixture is quenched with ice. The supernatant liquid is decanted, and the residue is dissolved in ethyl acetate (250 ml). The solution is dried over anhydrous magnesium sulfate and concentrated to a glass. Purification by passage through a short column of silica gel with 4:1 hexane:ethyl acetate as the eluent affords 19.8 g (85% yield) of the title compound, a white glass.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2.5 hours
  3. customThe reaction mixture is quenched with ice
  4. customThe supernatant liquid is decanted
  5. dissolutionthe residue is dissolved in ethyl acetate (250 ml)
  6. dry with materialThe solution is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated to a glass
  8. customPurification by passage through a short column of silica gel with 4:1 hexane

Sources & evidence

ORD record
ord-981d303beea04be3ad54e9f5a918b95d
Source dataset
uspto-grants-1991_05
Patent number
US05019613

Reaction notes

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