Diethyl Ether → 3-Chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile

HRID 1622411Notes

Reaction equation

HRID 1622411 reaction equation
F[C:2]1[CH:3]=[C:4]([Cl:10])[CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(OCC)C>CS(C)=O.Cl>[Cl:10][C:4]1[CH:5]=[C:6]([CH:9]=[C:2]([N:15]2[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]2)[CH:3]=1)[C:7]#[N:8]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 531671-MethylpiperazineHCID 27348413-Chloro-5-fluorobenzonitrile

Product 1

HCID 591389873-Chloro-5-(4-methyl-piperazin-1-yl)-benzonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

5-Fluoro-3-chloro-benzonitrile (Ig, 6.4 mmol) was dissolved in DMSO (20 ml) followed by addition OfK2CO3 (1.3 g, 9.6 mmol) and 1-methyl piperazine (1.4 ml, 12.8 mmol). The reaction mixture was heated at 80° C. for 20 hours. Diethyl ether was added to the crude material (10 ml) then acidified with IN HCl. A precipitate was filtered off from the crude reaction mixture to give 3-chloro-5-(4-methyl-ρiρerazin-1-yl)-benzonitrile (1.4 g, 93% yield) as a white solid (LC/MS: Rt 1.83 [M+H]+ 236, acidic method).

Workup

  1. filtrationA precipitate was filtered off from the crude
  2. customreaction mixture

Sources & evidence

ORD record
ord-9f683d136e994013b8fdc6d37775a1ae
Source dataset
uspto-grants-2014_07
Patent number
US08778936B2

Reaction notes

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