Piperazine → 3-Chloro-4-(piperazin-1-yl)benzonitrile

HRID 386531

Reaction equation

HRID 386531 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 1455253-Chloro-4-fluorobenzonitrile

Product 1

HCID 193671133-Chloro-4-(piperazin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-chloro-4-fluoro-benzonitrile (236 mg, 1.52 mmoles), piperazine (784 mg, 9.1 mmoles) and potassium carbonate (276 mg, 2 mmoles) in acetonitrile (5 mL) was heated to 100° C. overnight. The mixture was cooled, filtered and the filtrate concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 0-5% 2N methanolic ammonia in DCM) to provide the title compound. MS(APCI+) m/z 222 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe crude residue was purified by column chromatography (silica gel, 0-5% 2N methanolic ammonia in DCM)

Sources & evidence

ORD record
ord-33e105e4e80148a6aee6147e3a665670
Source dataset
uspto-grants-2013_02
Patent number
US08372841B2

Linked notes

Loading…