Sodium Hydroxide → N-[[(4-carboxyphenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine

HRID 4366Notes

Reaction equation

HRID 4366 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][N:15]2[CH2:20][CH:19]=[CH:18][CH2:17][CH2:16]2)=[O:13])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO.C(Cl)(Cl)Cl>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([NH:14][N:15]2[CH2:16][CH:17]=[CH:18][CH2:19][CH2:20]2)=[O:13])=[CH:9][CH:10]=1)([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13534723N-[[(4-methoxycarbonylphenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine

Product 1

HCID 13534725N-[[(4-carboxyphenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridineYield 56.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of N-[[(4-methoxycarbonylphenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine (1.21 g) in a mixture of methanol (30 ml) and chloroform (30 ml) was added. 1N sodium hydroxide (10 ml) and the mixture was stirred at ambient temperature for 18 hours. After evaporation of the solvent, the residue was extracted with chloroform (20 ml×3). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (40 g) eluting with chloroform, to give N-[[(4-carboxyphenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine (0.65 g).

Workup

  1. additionwas added
  2. customAfter evaporation of the solvent
  3. extractionthe residue was extracted with chloroform (20 ml×3)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (40 g)
  8. washeluting with chloroform

Sources & evidence

ORD record
ord-824d03c3210447cc84bae0d08c4e9730
Source dataset
uspto-grants-1988_02
Patent number
US04725608

Reaction notes

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