Dimethyl Sulfoxide → 1-(3-Cyanophenyl)piperazine

HRID 551290Notes

Reaction equation

HRID 551290 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CS(C)=O>O>[C:5]([C:4]1[CH:3]=[C:2]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=1)#[N:6]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4837PiperazineHCID 678803-Fluorobenzonitrile

Product 1

HCID 114809021-(3-Cyanophenyl)piperazineYield 143.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-fluorobenzonitrile (3.0 g, 25 mmol), piperazine (11.8 g, 137 mmol) and dimethylsulphoxide (20 ml) is heated at 100° C. for 48 hours under an atmosphere of nitrogen. The reaction mixture is then cooled, poured into water (200 ml) and the resultant precipitate collected. This solid is chromatographed on silica gel (dichloromethane) to give the title compound as a white solid (6.7 g). 1H NMR (DMSO, 500 MHz) δ7.15-7.40 (m, 4H), 3.28 (m, 3H), 3.12 (m, 1H), 2.80 (m, 1H), 2.59 (m, 3H).

Workup

  1. temperatureThe reaction mixture is then cooled
  2. customthe resultant precipitate collected
  3. customThis solid is chromatographed on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-54a39dc3799e48f296756f3420669cff
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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