Phenyl isocyanate → N-[4-(1,4-Diazabicyclo[3.2.2]non-4-yl)phenyl]-N′-phenylurea

HRID 1443767Notes

Reaction equation

HRID 1443767 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)[CH2:3][CH2:2]2.[C:17]1([N:23]=[C:24]=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:24]([NH:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:25])=[CH:12][CH:11]=1)[CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67441600HCID 67441600, compound

Product 1

HCID 11151855N-[4-(1,4-Diazabicyclo[3.2.2]non-4-yl)phenyl]-N′-phenylurea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(1,4-diaza-bicyclo[3.2.2]non-4-yl)-phenylamine (0.43 g, 2.0 mmol), phenylisocyanate (0.29 ml, 2.5 mmol) and methanol (60 ml) was stirred at room temperature for 40 hours. The mixture was evaporated and diethylether (30 ml) was added, the precipitate was filtered. The product was isolated. Yield 0.23 g (34%). Mp. 145° C. (dec).

Workup

  1. customThe mixture was evaporated
  2. additiondiethylether (30 ml) was added
  3. filtrationthe precipitate was filtered
  4. customThe product was isolated

Sources & evidence

ORD record
ord-a2b8bab0afc84787a505920544b005db
Source dataset
uspto-grants-2010_02
Patent number
US07662808B2

Reaction notes

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