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

HRID 882722Notes

Reaction equation

HRID 882722 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 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-55d55093202e49f5b44505b2745318b6
Source dataset
uspto-grants-2012_08
Patent number
US08236793B2

Reaction notes

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