Piperazine → 2-[1-(2-Methoxyphenyl)ethoxy]-6-(1-piperazinyl)pyrazine

HRID 1296650Notes

Reaction equation

Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[CH3:10])[N:3]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.ClCCl>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:9]([O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:3]=1)[CH3:10]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of the product from step 1 above (0.93 g, 3.53 mmol) piperazine (0.88 g, 10.2 mmol) and K2CO3 (0.49 g, 3.53 mmol) in acetonitrile (7 mL) was heated in a sealed pyrex flask at 90° C. for 6.5 h. The reaction mixture was diluted with dichloromethane, filtered and concentrated in vacuo. The semi-solid residue was purified by silica gel chromatography (13×4 cm) using CHCl3/MeOH (9:1) as eluent. Solvents were evaporated off and the remaining oil was redissolved in CHCl3, filtered through a short plug of alumina, covered with K2CO3, using CHCl3 as eluent. Solvent removal in vacuo gave 0.74 g (67%) of the title compound as a beige oil. HRMS m/z calcd for C17H22N4O2 (M)+ 314.1743, found 314.1733. Anal. (C17H22N4O2.0.5H2O) C, H, N.

Workup

filtrationfiltered
concentrationconcentrated in vacuo
customThe semi-solid residue was purified by silica gel chromatography (13×4 cm)
customSolvents were evaporated off
dissolutionthe remaining oil was redissolved in CHCl3
filtrationfiltered through a short plug of alumina
customSolvent removal in vacuo

Sources & evidence

ORD record: ord-f874605d6d204a1f86b765c62fbc3b2a
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247633B2

Reaction notes

Loading…