Triethylamine → 5-Bromo-2-(4-methyl-piperazin-1-yl)-benzonitrile

HRID 1052291Notes

Reaction equation

HRID 1052291 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[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(N(CC)CC)C>C(O)CCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:15]2[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 595583365-Bromo-2-(4-methyl-piperazin-1-yl)-benzonitrileYield 92.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-bromo-2-fluorobenzonitrile (0.20 g, 1.0 mmol), 1-methylpiperizine (0.15 g, 1.5 mmol) and triethylamine (0.20 g, 2.0 mmol) in 1-butanol (3.0 mL) was heated at 140° C. for 2 hours. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate, washed with water, brine, dried over Na2SO4, filtered and concentrated to provide the desired product (0.26 g, 92%). LCMS calculated for C12H15BrN3(M+H)+: m/z=280.0. Found 280.0.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4084e5b7adf443d9bdc6568412fe4013
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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