1-(Cyclopropylmethyl)piperazine → 4-(6-(4-Cyclopropylmethylpiperazin-1-yl)-pyridin-3-yl)-benzonitrile

HRID 80929

Reaction equation

HRID 80929 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:3][CH2:2]1.Cl[C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1>>[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:12]3[N:17]=[CH:16][C:15]([C:18]4[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 9658751-(Cyclopropylmethyl)piperazineHCID 497618214-(6-Chloro-3-pyridinyl)benzonitrile

Product 1

HCID 580066674-(6-(4-Cyclopropylmethylpiperazin-1-yl)-pyridin-3-yl)-benzonitrileYield 43%

Conditions

Temperature
140 °C

Procedure

1-Cyclopropylmethyl-piperazine (13 g, 94 mmol) was mixed with 4-(6-cloro-pyridin-3-yl)benzonitrile (5 g, 23 mmol). The mixture was heated at 140° C. for 1.5 hours. The mixture was cooled to rt and purified by column chromatography (EtOAc:petrolether=1:1) on silica gel to give 2.7 g (43%) of 4-[6-(4-cylopropylmethyl-piperazin-1-yl)-pyridin-3-yl]-benzonitrile.

Workup

  1. temperatureThe mixture was cooled to rt
  2. custompurified by column chromatography (EtOAc:petrolether=1:1) on silica gel

Sources & evidence

ORD record
ord-452190f306444fa498e29bad985dfcff
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Linked notes

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