Morpholine → HCID 14076582, compound

HRID 649429Notes

Reaction equation

HRID 649429 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([C:9]([C:19]#[N:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10](Cl)=[O:11])[CH3:8]>C(OCC)C>[C:19]([C:9]([CH2:7][CH3:8])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:11])#[N:20]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 12625035α-Cyano-α-ethylbenzeneacetyl chloride

Product 1

HCID 14076582HCID 14076582, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

8.7 g (0.1 mole) of morpholine are dissolved in 20 ml of dry diethyl ether, and a solution of 10.5 g (0.05 mole) of 2-ethyl-2-phenyl-cyanoacetyl chloride in 20 ml of dry diethyl ether are added dropwise under cooling with ice (at a temperature below 10° C.). The reaction mixture is refluxed for 30 minutes, then cooled and washed with water. The organic phase is separated, washed in succession with 5% aqueous sodium carbonate solution, 2n aqueous hydrochloric acid and water, dried over magnesium sulfate, and evaporated. 11.4 g (89%) of 2-cyano-2-ethyl-2-phenylacetic acid morpholide are obtained; m.p.: 88°-90° C.

Workup

  1. temperatureunder cooling with ice (at a temperature below 10° C.)
  2. temperatureThe reaction mixture is refluxed for 30 minutes
  3. temperaturecooled
  4. washwashed with water
  5. customThe organic phase is separated
  6. washwashed in succession with 5% aqueous sodium carbonate solution, 2n aqueous hydrochloric acid and water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-fa7b3dee75584635b29dd3738cf00ec5
Source dataset
uspto-grants-1988_04
Patent number
US04740228

Reaction notes

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