Water → N-(1-methoxycarbonylpiperidin-4-yl)-N'-(4-fluorophenyl)urea

HRID 49787Notes

Reaction equation

HRID 49787 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:25]([O:27][CH3:28])=[O:26].O>O1CCCC1.C(OCC)(=O)C>[CH3:28][O:27][C:25]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[O:9])[CH2:3][CH2:2]1)=[O:26]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 16781536283167-30-6

Product 1

HCID 9796177N-(1-methoxycarbonylpiperidin-4-yl)-N'-(4-fluorophenyl)urea

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(piperidin-4-yl)-N′-(4-fluorophenyl)urea (0.3 g) in tetrahydrofuran (4 ml) were added in turn pyridine (0.28 ml), methyl chloroformate (98 μl) and catalytic amount of N,N-dimethylaminopyridine at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 2 hours. The reaction mixture was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine, and dried over magnesium sulfate. Evaporation under reduced pressure gave a residue, which was triturated with diisopropyl ether to give N-(1-methoxycarbonylpiperidin-4-yl)-N′-(4-fluorophenyl)urea (0.312 g).

Workup

  1. washThe separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation under reduced pressure
  4. customgave a residue, which
  5. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-54fccd73dcba46ffa30693578c68994e
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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