N-(3-Cyanophenyl)-N'-(1-benzylpiperidin-4-yl)cycloheptylurea → N-(3-Cyanophenyl)-N'-(piperidin-4-yl)cycloheptylurea

HRID 1059526Notes

Reaction equation

HRID 1059526 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16](CC3C=CC=CC=3)[CH2:15][CH2:14]2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C(O)C.C1CCCCC=1.[OH-].[Pd+2].[OH-]>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 1

HCID 53879433N-(3-Cyanophenyl)-N'-(1-benzylpiperidin-4-yl)cycloheptylurea

Product 1

HCID 54268872N-(3-Cyanophenyl)-N'-(piperidin-4-yl)cycloheptylurea

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

N-(3-Cyanophenyl)-N′-(1-benzylpiperidin-4-yl)cycloheptylurea (0.1 g 0.26 mmol) was dissolved in ethanol (10 ml) and cyclohexene (2 ml). Palladium hydroxide catalyst (0.05 g) was added and the reaction was heated at reflux under a nitrogen atmosphere. After 30 min the reaction was allowed to cool to ambient temperature, filtered and concentrated to give a viscous oil. The crude product was purified by flash chromatography on silica gel by eluting with methylene chloride:methanol 85:15 with 3% triethylamine. The product, N-(3-cyanophenyl)-N′-(piperidin-4-yl)cycloheptylurea, was concentrated to give an oil which crystallized from ethyl ether (0.05 g, 48%, mp 157-8° C.); LRMS (M+H)+ m/z 299; 1H NMR (CDCl3): 7.5-7.3(m, 4H), 4.05(m, 1H), 3.60(m, 2H), 3.32(m, 2H), 3.17(m, 2H), 2.72(m, 2H), 2.0-1.6(m, 8H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under a nitrogen atmosphere
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a viscous oil
  6. customThe crude product was purified by flash chromatography on silica gel
  7. washby eluting with methylene chloride:methanol 85:15 with 3% triethylamine
  8. concentrationThe product, N-(3-cyanophenyl)-N′-(piperidin-4-yl)cycloheptylurea, was concentrated
  9. customto give an oil which
  10. customcrystallized from ethyl ether (0.05 g, 48%, mp 157-8° C.)

Sources & evidence

ORD record
ord-85696c71a7004b68aef8069799389375
Source dataset
uspto-grants-2003_02
Patent number
US06521614B1

Reaction notes

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