Cyanogen Bromide → HCID 58625156, compound

HRID 390246Notes

Reaction equation

HRID 390246 reaction equation
[CH:1]1([N:7]([CH3:30])[CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]2[CH:14]=[C:15]([C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:23])[CH:16]=[CH:17][C:18]=2[N+:19]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:31]#[C:32]Br>C(O)C>[NH2:31][C:32]1[N:11]([CH2:10][CH2:9][CH2:8][N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH3:30])[CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[C:15]([C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:23])[CH:14]=2)[N:19]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 68614275HCID 68614275, compound

Product 1

HCID 58625156HCID 58625156, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (3-{[3-(Cyclohexyl-methyl-amino)-propylamino]-methyl}-4-nitro-phenyl)-phenyl-methanone (0.0037 mol) in ethanol (40 mL) was stirred at room temperature. Cyanogen bromide (0.0055 mol) was added, and the reaction mixture was stirred and refluxed for 4 hours, then cooled and the resulting precipitate was filtered off and dried. This fraction was recrystallized from CH3CN, then filtered off and recrystallized from methanol, filtered off, washed with diisopropyl ether, then dried to yield the title compound as a solid.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperaturerefluxed for 4 hours
  3. temperaturecooled
  4. filtrationthe resulting precipitate was filtered off
  5. customdried
  6. customThis fraction was recrystallized from CH3CN
  7. filtrationfiltered off
  8. customrecrystallized from methanol
  9. filtrationfiltered off
  10. washwashed with diisopropyl ether
  11. customdried

Sources & evidence

ORD record
ord-522a65d686a5403d91d04064c2a8e44a
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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