1-(2-Fluorophenyl)piperazine → HCID 72548960, compound

HRID 1022436Notes

Reaction equation

HRID 1022436 reaction equation
Cl[C:2]1[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][N:11]([CH3:12])[C:4]=2[CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C(Cl)Cl.CO>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][N:23]([C:2]2[NH:7][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][N:11]([CH3:12])[C:4]=3[CH:3]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 705291-(2-Fluorophenyl)piperazineHCID 86704558HCID 86704558, compound2×

Product 1

HCID 72548960HCID 72548960, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-chloro-1-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one (Intermediate G) (17 mg, 0.09 mmol) and 1-(2-fluorophenyl)piperazine (140 mg, 0.77 mmol) was heated at 140° C. in a sealed tube overnight. Flash chromatography (20/1 methylene chloride/methanol) afforded 6-[4-(2-fluoro-phenyl)-piperazin-1-yl]-1-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (20 mg, 65.8%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.1 (d, J=4.77 Hz, 4H) 3.2-3.3 (m, 4H) 3.6 (s, 3H) 5.8 (s, 1H) 6.3 (d, J=3.01 Hz, 1H) 6.9 (d, J=3.01 Hz, 1H) 7.0-7.0 (m, 1H) 7.1-7.2 (m, 3H) 10.6 (s, 1H). LC-MS calcd. for C18H20FN4O [(M+H)+] 327, obsd. 327.1.

Sources & evidence

ORD record
ord-4a2ec81ae3074783b3cf2f4374c35352
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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