Ethyl chloroformate → HCID 13377594, compound

HRID 1703161Notes

Reaction equation

HRID 1703161 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[C:11]1[CH2:16][CH2:15][N:14](C)[CH2:13][CH2:12]1.ClC(OCC)=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[C:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 214822HCID 214822, compound

Product 1

HCID 13377594HCID 13377594, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

43 g 4-(2,2-dimethylindane-1-ylidene)-1-methyl-piperidine and 65 g ethyl chloroformate in 800 ml toluene are refluxed for 3 hours. After cooling, the solution is washed with 1 N hydrochloric acid and water, dried over magnesium sulfate and the toluene distilled off. The oily residue is then refluxed for 6 hours in 90 ml n-butanol and 9 g potassium hydroxide. The reaction mixture is cooled, filtered, diluted with ether and shaken out with water until neutral. The organic phase is then dried over magnesium sulfate and evaporated, to give the title compound as the hydrogenofumarate: m.p. 200°-202°.

Workup

  1. temperatureAfter cooling
  2. washthe solution is washed with 1 N hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. distillationthe toluene distilled off
  5. temperatureThe oily residue is then refluxed for 6 hours in 90 ml n-butanol
  6. temperatureThe reaction mixture is cooled
  7. filtrationfiltered
  8. additiondiluted with ether
  9. dry with materialThe organic phase is then dried over magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-d589aafac1cf4836a0c6670d16c45908
Source dataset
uspto-grants-1982_09
Patent number
US04351838

Reaction notes

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