Triethylamine → FR 64822

HRID 2309182Notes

Reaction equation

HRID 2309182 reaction equation
O([C:8]([NH:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:9])C1C=CC=CC=1.Cl.[NH2:18][N:19]1[CH2:24][CH:23]=[CH:22][CH2:21][CH2:20]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:14]1[CH:13]=[CH:12][C:11]([NH:10][C:8]([NH:18][N:19]2[CH2:20][CH:21]=[CH:22][CH2:23][CH2:24]2)=[O:9])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterHCID 193760471,2,3,6-Tetrahydropyridin-1-amine hydrochloride

Product 1

HCID 128144FR 64822Yield 45.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-(phenoxycarbonylamino)pyridine (4.284 g), N-amino-1,2,3,6-tetrahydropyridine hydrochloride (4.038 g) and triethylamine (3.036 g) in chloroform (70 ml) was refluxed for 20 hours. After evaporation of chloroform, the residue was extracted with ethyl acetate (200 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (52 g) using chloroform to give N-[(4-pyridylcarbamoyl)amino]-1,2,3,6-tetrahydropyridine (2.005 g).

Workup

  1. customAfter evaporation of chloroform
  2. extractionthe residue was extracted with ethyl acetate (200 ml)
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (52 g)

Sources & evidence

ORD record
ord-7f4b050aa42f4c338019c48ee67c3657
Source dataset
uspto-grants-1987_09
Patent number
US04694004

Reaction notes

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