Cyanogen Bromide → HCID 21101963, compound

HRID 1353403Notes

Reaction equation

HRID 1353403 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[N:23]#[C:24]Br>CCO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:24]#[N:23])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 7383897-Chloro-4-(piperazin-1-yl)quinoline

Product 1

HCID 21101963HCID 21101963, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 7-Chloro-4-(piperazin-1-yl)quinoline (496 mg, 2.0 mmol) and NaHCO3 (504 mg, 6.0 mmol) in EtOH is treated with cyanogen bromide (5 M in MeCN, 440 μL, 2.2 mmol) and stirred at room temp. for 2 h. The solvent is removed, and the residue suspended in CH2Cl2 and filtered. The filtrate is concentrated, and the residue is purified by column chromatography with hexane-EtOAc giving 221 mg of the product as a colorless solid.

Workup

  1. customThe solvent is removed
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated
  4. customthe residue is purified by column chromatography with hexane-EtOAc giving 221 mg of the product as a colorless solid

Sources & evidence

ORD record
ord-bf21191589a6460e93b4d78500ec55e5
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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