Sodium Iodide → ethyl 4-{2-[1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}piperazine carboxylate

HRID 220006Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:9]=[C:8]([CH3:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[N:6]=1.[N:19]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C)C=O>[Cl:18][C:13]1[CH:12]=[C:11]([N:7]2[C:8]([CH3:10])=[CH:9][C:5]([O:4][CH2:3][CH2:2][N:22]3[CH2:21][CH2:20][N:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23]3)=[N:6]2)[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 3-(2-chloroethoxy)-1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazole (0.2 g, 0.65 mmol), ethyl piperazine-1-carboxylate (0.113 g, 0.72 mmol), K2CO3 (270 mg, 1.96 mmol) and NaI (98 mg, 0.65 mmol) in dry dimethylformamide (6 ml) was warmed overnight at 85° C., and then an additionally 16 hrs at 95° C., in a dry nitrogen atmosphere. Solvents were evaporated in vacuo and the crude residue partitioned in water/ethyle acetate. The combined organic extracts were washed with water, dried on Na2SO4 and concentrated in vacuo to obtain a crude oil, which was purified by column chromatography on silica gel (ethyl acetate/petroleum ether 8:2) yielding 69 mg of ethyl 4-{2-[1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}piperazine carboxylate as a colourless oil

Workup

customan additionally 16 hrs
customat 95° C.
customSolvents were evaporated in vacuo
customthe crude residue partitioned in water/ethyle acetate
washThe combined organic extracts were washed with water
customdried on Na2SO4
concentrationconcentrated in vacuo
customto obtain a crude oil, which
customwas purified by column chromatography on silica gel (ethyl acetate/petroleum ether 8:2)

Sources & evidence

ORD record: ord-228f5cb8ac3c4e298a2cfc832953b3f1
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202872B2

Reaction notes

Loading…