1-(2-Fluorophenyl)piperazine → ethyl 1-(2-(4-(2-fluorophenyl)piperazin-1-yl)-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate

HRID 77365

Reaction equation

Cl.C(O[C:5](=[NH:18])[CH2:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])C.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(O)C>[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([C:5](=[NH:18])[CH2:6][N:7]2[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of ethyl 1-(2-ethoxy-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate hydrochloride (950 mg, 3.46 mmol) and 1-(2-fluorophenyl)piperazine (1.87 g, 10.4 mmol) in ethanol (5 mL) was heated at 55° C. overnight. At this time, the reaction was concentrated in vacuo. Reverse phase column chromatography (0-100% acetonitrile/water) afforded ethyl 1-(2-(4-(2-fluorophenyl)piperazin-1-yl)-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate (1.1 g, 85.4%) as a white solid. LC-MS calcd. for C20H26N4O2 [(M+H)+] 373, obsd. 373.0.

Workup

concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-dba85c6aabde48c7b3e8d9aed4842d64
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841299B2

Linked notes

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