Reaction #640589

ord-e83eb20cb7d14388bd92d7273355ee1f

Reaction equation

N#CBr
cyanogen bromide
N[C@@H]1CCCC[C@H]1N
(±)-trans-1,2-cyclohexanediamine
O=Cc1ccc(F)c(F)c1
3,4-difluorobenzaldehyde
N=C1N(Cc2ccc(F)c(F)c2)[C@@H]2CCCC[C@H]2N1Cc1ccc(F)c(F)c1
title compound
N=C1N(Cc2ccc(F)c(F)c2)[C@@H]2CCCC[C@H]2N1Cc1ccc(F)c(F)c1
(±)-trans-1,3-Bis-(3,4-difluoro-benzyl)octahydro-benzoimidazol-2-ylideneamine

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe reaction mixture was evaporated to dryness
  2. 2
    Washthe crude product washed with ether
  3. 3
    Otherrecrystallized from MeOH

Procedure

The title compound was prepared from (±)-trans-1,2-cyclohexanediamine and 3,4-difluorobenzaldehyde by Procedure C. After reacting with cyanogen bromide, the reaction mixture was evaporated to dryness and the crude product washed with ether and recrystallized from MeOH to give the title compound as the hydrogen bromide salt (mp 238-240° C.). MS (ES+) m/z 392 ([M+1]+, 100).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08048877B2uspto-grants-2011_11