Morpholine → HCID 14076582, compound

HRID 649432Notes

Reaction equation

HRID 649432 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:9]([C:11]([CH2:21][CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12](Cl)=[O:13])#[N:10]>C(Cl)Cl>[C:9]([C:11]([CH2:21][CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:13])#[N:10]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 14798Sodium HydroxideHCID 12625035α-Cyano-α-ethylbenzeneacetyl chloride

Product 1

HCID 14076582HCID 14076582, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4.4 g (0.05 mole) of morpholine are dissolved in 50 ml of methylene chloride, 20 ml of a 20% aqueous sodium hydroxide solution are added to it, and the mixture is cooled to a temperature below -10° C. with salted ice. 10.5 g (0.05 mole) of 2-cyano-2-ethyl-2-phenylacetyl chloride are added to the mixture in portions, under vigorous stirring. The reaction mixture is stirred at 0° C. for one hour, thereafter the phases are separated from each other, the organic phase is washed twice with dilute aqueous hydrochloric acid, dried over a mixture of anhydrous magnesium sulfate and potassium carbonate, filtered, and the solvent is evaporated. 10.3 g (81%) of 2-cyano-2-ethyl-2-phenylacetic acid morpholide are obtained; m.p.: 87°-89.5° C.

Workup

  1. temperaturethe mixture is cooled to a temperature below -10° C. with salted ice
  2. customthe phases are separated from each other, the organic phase
  3. washis washed twice with dilute aqueous hydrochloric acid
  4. dry with materialdried over a mixture of anhydrous magnesium sulfate and potassium carbonate
  5. filtrationfiltered
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-c58fa94ba65e4c93b8106b19fe82e23f
Source dataset
uspto-grants-1988_04
Patent number
US04740228

Reaction notes

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