Piperazine → 2-(Piperazin-1-yl)-4-trifluoromethylbenzonitrile

HRID 1592747Notes

Reaction equation

HRID 1592747 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:8]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]>CS(C)=O.CCOC(C)=O>[C:10]([C:9]1[CH:12]=[CH:13][C:14]([C:16]([F:17])([F:18])[F:19])=[CH:15][C:8]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)#[N:11]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 179523242-(Piperazin-1-yl)-4-trifluoromethylbenzonitrileYield 96.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of piperazine (13.7 g, 159 mmol) in 20 mL DMSO was added 2-fluoro-4-trifluoromethylbenzonitrile (10 g, 52.9 mmol). After stirring overnight, the solution was diluted with 200 mL of EtOAc, washed with water and brine, and then dried (Na2SO4), filtered and concentrated to afford about 13.0 g (51.1 mmol, 96%) of 4-(2-cyano-5-trifluoromethyl-phenyl)piperazine. LRMS (ESI+): 256.1 [M+1]. The tide compound was prepared from 4-(2-cyano-5-trifluoromethyl-phenyl)piperazine in the same manner as described in Preparation 67A except that dimethyl amine was used to displace the mesylate. LRMS (ESI+): 388.1 [M+1]

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-85ec3716fef7426f992015cf15a51efb
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

Loading…