Triethylamine → N-[[(4-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridine

HRID 4363Notes

Reaction equation

HRID 4363 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([NH:6][C:7]([O:9]C2C=CC=CC=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:19][N:20]1[CH2:25][CH:24]=[CH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7]([NH:19][N:20]2[CH2:21][CH:22]=[CH:23][CH2:24][CH2:25]2)=[O:9])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10751974Phenyl N-(4-fluorophenyl)carbamateHCID 193760471,2,3,6-Tetrahydropyridin-1-amine hydrochloride

Product 1

HCID 13534699N-[[(4-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridineYield 45.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-fluoro-N-phenoxycarbonylaniline (2.29 g), N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylamine (1.02 g) in chloroform (25 ml) was refluxed for 20 hours. After evaporation of chloroform, the residue was extracted with ethyl acetate (100 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (20 g) using chloroform as an eluent to give N-[[(4-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridine (1.05 g). mp: 156°-157° C.

Workup

  1. customAfter evaporation of chloroform
  2. extractionthe residue was extracted with ethyl acetate (100 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 (20 g)

Sources & evidence

ORD record
ord-cc5f2343b0b2464494f03f96f151a07a
Source dataset
uspto-grants-1988_02
Patent number
US04725608

Reaction notes

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