HCID 20569917, compound → N-Butyl-N'-piperidin-4-ylurea

HRID 1577841Notes

Reaction equation

HRID 1577841 reaction equation
Cl.[CH2:2]([NH:6][C:7](=[O:15])[NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH3:5].[H][H]>C(O)C.O.[Rh]>[CH2:2]([NH:6][C:7](=[O:15])[NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 20569917HCID 20569917, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12608579N-Butyl-N'-piperidin-4-ylureaYield 19.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 3-n-butyl-1-(4-pyridyl)urea hydrochloride (37.4 g) in ethanol-water (1:1, 400 ml) containing 5% rhodium/alumina catalyst (10 g) was hydrogenated (50°, 750 psi) until no further uptake of hydrogen occurred. The catalyst was then removed by filtration and the solvent evaporated to leave an oil which partially solidified on storage at 0°. The solid was separated, treated with base, extracted with chloroform/n-butanol, the extracts evaporated and the residue recrystallized twice from ethyl acetate to give 3-n-butyl-1-(4-piperidyl)urea, (6.3 g), m.p. 132°-134°.

Workup

  1. custom(50°, 750 psi)
  2. customThe catalyst was then removed by filtration
  3. customthe solvent evaporated
  4. customto leave an oil which
  5. custompartially solidified on storage at 0°
  6. customThe solid was separated
  7. additiontreated with base
  8. extractionextracted with chloroform/n-butanol
  9. customthe extracts evaporated
  10. customthe residue recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-98bd7d0e70a547579e4503920b53fe44
Source dataset
uspto-grants-1981_09
Patent number
US04289772

Reaction notes

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