1-(4-Pyridyl)piperazine → HCID 18918452, compound

HRID 743838Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:17][CH:16]=1>C(#N)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:20]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 30 °C

Procedure

1-(4-Pyridyl)piperazine (1.63 g) was dissolved in warm acetonitrile (25 ml), the solution cooled to 30° C. and with stirring, a solution of methyl 4-(4-bromomethylphenyl)butyrate in acetonitrile (5 ml) added. After 30 minutes the resulting precipitate was removed by filtration and the filtrate concentrated in vacuo to give a yellow oil. Purification by flash chromatography on silica, eluting with 0 to 4% v/v methanol/dichloromethane gave a solid. Trituration with ether and removal of the insoluble solid gave a clear solution. Concentration of this solution gave the title compound, 0.90 g, as a white fluffy solid: m.p. 126°-127° C.; NMR (d6DMSO) δ8.14 (2H, d), 7.24 (2H, d), 7.14 (2H, d), 6.77 (2H, d), 3.59 (3H, s), 3.48 (2H, s), 3.30 (4H, t), 2.59 (2H, t), 2.47 (4H, t), 2.32 (2H, t), 1.63 (2H, m); m/e 354 (M+H)+ ; calculated for C21H27N3O2.0.25H2O: C, 70.4; H, 7.7; N, 11.7. found: C, 70.6; H, 7.6; N, 11.7%.

Workup

customAfter 30 minutes the resulting precipitate was removed by filtration
concentrationthe filtrate concentrated in vacuo
customto give a yellow oil
customPurification by flash chromatography on silica
washeluting with 0 to 4% v/v methanol/dichloromethane
customgave a solid
customTrituration with ether and removal of the insoluble solid
customgave a clear solution

Sources & evidence

ORD record: ord-bfe8a41dc8d54500a4728e5c0a10872b
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556977

Reaction notes

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