Ethyl Nicotinate → HCID 375175, compound

HRID 1450696Notes

Reaction equation

HRID 1450696 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1>O>[CH:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:1]([CH2:6][CH2:7][CH2:2][CH2:3][NH2:4])=[O:9])[CH:7]=1

Participants

3

Reactant 1

HCID 69188Ethyl Nicotinate

Product 1

HCID 375175HCID 375175, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The first crop of solid was recrystallized by adding it to about 200 mL of hot isopropyl alcohol and adding 6M HCl slowly to the boiling mixture until all of the solid dissolved (about 5 mL of HCl was added). After cooling the solution in the refrigerator, 3.26 g of anabaseine dihydrochloride was collected (mp 175°-180° C., decomp). Anabaseine dihydrochloride was prepared in 56% overall yield based on the moles of ethyl nicotinate used. Since the dry crystalline solid product is not hygroscopic, but the wet solid may pick up water after filtration, filtration should be performed, for example, under nitrogen atmosphere.

Workup

  1. customThe first crop of solid was recrystallized
  2. additionby adding it to about 200 mL of hot isopropyl alcohol
  3. additionadding 6M HCl slowly to the boiling mixture until all of the solid
  4. dissolutiondissolved
  5. addition(about 5 mL of HCl was added)
  6. temperatureAfter cooling the solution in the refrigerator, 3.26 g of anabaseine dihydrochloride
  7. customwas collected (mp 175°-180° C., decomp)
  8. customoverall yield
  9. filtrationafter filtration, filtration

Sources & evidence

ORD record
ord-910d059b06054c5a9fb9179ddec7adcd
Source dataset
uspto-grants-1997_02
Patent number
US05602257

Reaction notes

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