Dimethyl Sulfoxide → 6-(4-Isopropylpiperazin-1-yl)nicotinonitrile

HRID 1887134Notes

Reaction equation

HRID 1887134 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.CS(C)=O.[CH:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:16])[CH3:15]>O>[CH:14]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=2)[CH2:19][CH2:18]1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 780131-IsopropylpiperazineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 434217446-(4-Isopropylpiperazin-1-yl)nicotinonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloropyridine-5-carbonitrile (5.0 g, 36.1 mmol), DMSO (10 mL) and 1-isopropylpiperazine (10.7 mL, 75.8 mmol) was stirred under an atmosphere of nitrogen and heated on a 100° C. oil-bath for 3 h. The reaction mixture was allowed to cool, and then poured into cold water (500 mL). The solid was isolated by filtration, washed with water and dried to give 6.8 g (82%) of 6-(4-isopropylpiperazin-1-yl)nicotinonitrile.

Workup

  1. temperatureto cool
  2. customThe solid was isolated by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c1a0cedd8fd84ac8a7383a8bdbc30bb1
Source dataset
uspto-grants-2013_08
Patent number
US08501739B2

Reaction notes

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