Triethylamine → HCID 20185950, compound

HRID 2309183Notes

Reaction equation

HRID 2309183 reaction equation
ClC([O:4][C:5](Cl)(Cl)Cl)=O.[NH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.Cl.[NH2:17][N:18]1[CH2:23][CH:22]=[CH:21][CH2:20][CH2:19]1.C(N(CC)CC)C>C(Cl)Cl>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][C:5]([NH:17][N:18]2[CH2:19][CH:20]=[CH:21][CH2:22][CH2:23]2)=[O:4])[CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 10426DiphosgeneHCID 193760471,2,3,6-Tetrahydropyridin-1-amine hydrochloride

Product 1

HCID 20185950HCID 20185950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-50 °C

Procedure

To a solution of trichloromethyl chloroformate (2.76 ml) in methylene chloride (200 ml) was added a solution of 3-aminopyridine (2.165 g) in methylene chloride (50 ml) and stirred for 2 hours at -50° C. The mixture was added to a mixture of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (3.096 g) and triethylamine (2.327 g) in methylene chloride (100 ml) and the resultant mixture was stirred at the same temperature. After stirring for 1 hour, the reaction mixture was allowed to warm to ambient temperature and stirred for 17 hours. After evaporation of methylene chloride, the residue was dissolved in water (50 ml) and the resultant aqueous solution was adjusted to pH 8.0-8.5 with sodium bicarbonate. The precipitate was removed by filtration and the filtrate was extracted with ethyl acetate (300 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (40 g) using chloroform. The fractions containing the desired compound were combined and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give N-[(3-pyridylcarbamoyl)amino]-1,2,3,6-tetrahydropyridine (1.62 g).

Workup

  1. stirringAfter stirring for 1 hour
  2. temperatureto warm to ambient temperature
  3. stirringstirred for 17 hours
  4. customAfter evaporation of methylene chloride
  5. dissolutionthe residue was dissolved in water (50 ml)
  6. customThe precipitate was removed by filtration
  7. extractionthe filtrate was extracted with ethyl acetate (300 ml)
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was chromatographed on silica gel (40 g)
  12. additionThe fractions containing the desired compound
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cf10606eff4e4f6aaf979809a3c27649
Source dataset
uspto-grants-1987_09
Patent number
US04694004

Reaction notes

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