Benzyl Chloride → HCID 19848614, compound

HRID 1608223Notes

Reaction equation

HRID 1608223 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]1[O:10][CH2:9][CH2:8][NH:7][CH2:6]1)#[N:2].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(C(C)=O)C>[C:1]([CH2:3][CH2:4][CH:5]1[O:10][CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)#[N:2]

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 19848620HCID 19848620, compound

Product 1

HCID 19848614HCID 19848614, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-(2-cyanoethyl)morpholine (5.4 g), benzyl chloride (5.4 g), potassium carbonate (5.4 g), potassium iodide (0.5 g), and methyl ethyl ketone (30 ml) is heated under reflux for 1 hour. After cooling, the reaction mixture is filtered and the filtrate is concentrated. The residue is dissolved in diethyl ether, and the solution is extracted with dilute hydrochloric acid. The extracts are basified with dilute aqueous sodium hydroxide solution and extracted with chloroform. The organic layer is dried over sodium sulfate and evaporated to give the title compound (8 g) as an oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. concentrationthe filtrate is concentrated
  6. dissolutionThe residue is dissolved in diethyl ether
  7. extractionthe solution is extracted with dilute hydrochloric acid
  8. extractionextracted with chloroform
  9. dry with materialThe organic layer is dried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-5eebdadcf58345f1af01e55b109ea6f2
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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