1-Methylpiperazine → 6-(4-Methyl-piperazin-1-yl)-4-o-tolyl-nicotinonitrile

HRID 1182374Notes

Reaction equation

Cl[C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH3:16])[C:5]([C:6]#[N:7])=[CH:4][N:3]=2)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 112 °C

Procedure

500 mg (2.1865 mmol) 6-chloro-4-o-tolyl-nicotinonitrile were dissolved in 10.0 ml toluene and heated to 112° C. At this temperature 2.19 g (21.865 mmol) 1-methylpiperazine were added, and the reaction mixture was stirred for further 60 minutes. The mixture was cooled down to 50° C. and concentrated under reduced pressure. 5 ml toluene were added to the obtained residue at a temperature of 20-25° C., followed by 900 mg sulfuric acid (95%). The organic phase was washed with 5 ml water. Evaporation in vacuo gave 520 mg of 6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinonitrile as a beige foam.

Workup

temperatureThe mixture was cooled down to 50° C.
concentrationconcentrated under reduced pressure
addition5 ml toluene were added to the obtained residue at a temperature of 20-25° C.
washThe organic phase was washed with 5 ml water
customEvaporation in vacuo

Sources & evidence

ORD record: ord-06fb25756e7b44cc85222404a74307b0
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288658B2

Reaction notes

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