Bicarbonate Ion → HCID 21405558, compound

HRID 972827Notes

Reaction equation

HRID 972827 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH3:9])[CH2:4][CH2:3]1.[N+:10]([C:13]1[CH:14]=[C:15]2[C:20](=O)[O:19][C:17](=[O:18])[C:16]2=[CH:22][CH:23]=1)([O-:12])=[O:11].C(=O)(O)[O-]>C(Cl)(Cl)Cl>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([N:1]2[C:20](=[O:19])[C:15]3=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:23][CH:22]=[C:16]3[C:17]2=[O:18])[CH2:3][CH2:4]1)[CH3:9]

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 2309764-Nitrophthalic acid anhydrideHCID 37349901-Ethylpiperidin-4-amine

Product 1

HCID 21405558HCID 21405558, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

6.50 Grams (0.05 mole) of 4-amino-N-ethyl piperidine and 9.65 grams (0.05 mole) of 4-nitrophthalic anhydride were dissolved in 150 milliliters of chloroform and the solution was stirred for an hour at room temperature. The chloroform was evaporated and the solid dissolved in 50 milliliters of acetic anhydride and the solution was refluxed for an hour. The acetic anhydride was evaporated off and the dark red residue treated with isopropyl alcohol and the solvent evaporated. The residue which was a gum was repeatly subjected to treatment with isopropyl alcohol and evaporation of the solvent until a crystalline solid was produced. The solid was taken up in chloroform and this was washed with sodium bicarbonate solution, then water and then brine until the aqueous layer was neutral. The chloroform extract was dried with magnesium sulphate, filtered and evaporated to give a solid. Microanalysis showed this to be impure and the bicarbonate washing was repeated as outlined above. The dried chloroform extract was evaporated off and the residue treated with ether to give 2.5 grams of the title compound as a yellow solid, m.p. 153°-155°.

Workup

  1. customThe chloroform was evaporated
  2. dissolutionthe solid dissolved in 50 milliliters of acetic anhydride
  3. temperaturethe solution was refluxed for an hour
  4. customThe acetic anhydride was evaporated off
  5. additionthe dark red residue treated with isopropyl alcohol
  6. customthe solvent evaporated
  7. customwas repeatly subjected to treatment with isopropyl alcohol and evaporation of the solvent until a crystalline solid
  8. customwas produced
  9. washthis was washed with sodium bicarbonate solution
  10. extractionThe chloroform extract
  11. dry with materialwas dried with magnesium sulphate
  12. filtrationfiltered
  13. customevaporated
  14. customto give a solid
  15. extractionThe dried chloroform extract
  16. customwas evaporated off
  17. additionthe residue treated with ether

Sources & evidence

ORD record
ord-eb369258ed62482391e322cce8c40b3b
Source dataset
uspto-grants-1977_10
Patent number
US04053615

Reaction notes

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