1-Methyl-1-(4-pyridylmethyl)-3-phenylurea → 1-Methyl-1-(4-piperidylmethyl)-3-cyclohexylurea

HRID 1164514Notes

Reaction equation

HRID 1164514 reaction equation
[CH3:1][N:2]([CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[H][H]>C(O)(=O)C.[Pt]=O>[CH3:1][N:2]([CH2:12][CH:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1)[C:3]([NH:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 205111981-Methyl-1-(4-pyridylmethyl)-3-phenylureaHCID 178418361HCID 178418361, compound

Product 1

HCID 205111921-Methyl-1-(4-piperidylmethyl)-3-cyclohexylureaYield 54.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

1-Methyl-1-(4-pyridylmethyl)-3-phenylurea (7.0 g) in glacial acetic acid (50 ml) was hydrogenated over platinum oxide at 60°/60 p.s.i. until uptake of hydrogen ceased. The catalyst was removed by filtration and the filtrate evaporated in vacuo. The resultant oil was basified with 5 N NaOH (to pH 12) and extracted with chloroform (2×50 ml). The combined extracts were dried (MgSO4) and evaporated with chloroform (2×50 ml). The combined extracts were dried (MgSO4) and evaporated to give 1-methyl-1-(4-piperidylmethyl)-3-cyclohexylurea as an oil (4.0 g). The n.m.r. and mass spectra were compatible with the required structure.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated in vacuo
  3. extractionextracted with chloroform (2×50 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated with chloroform (2×50 ml)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-28a56f0610ff4e2599e3656291c640c7
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

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