1-(2-Fluorophenyl)piperazine → HCID 72548961, compound

HRID 1022437Notes

Reaction equation

HRID 1022437 reaction equation
Cl[C:2]1[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][N:11]([CH2:12][CH3:13])[C:4]=2[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(Cl)Cl.CO>[CH2:12]([N:11]1[C:4]2[CH:3]=[C:2]([N:24]3[CH2:23][CH2:22][N:21]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[F:14])[CH2:26][CH2:25]3)[NH:7][C:6](=[O:8])[C:5]=2[CH:9]=[CH:10]1)[CH3:13]

Participants

4

Reactant 2

HCID 705291-(2-Fluorophenyl)piperazineHCID 86704560HCID 86704560, compound2×

Product 1

HCID 72548961HCID 72548961, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-chloro-1-ethyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one (Intermediate G) (16 mg, 0.081 mmol) and 1-(2-fluorophenyl)piperazine (160 mg, 0.888 mmol) was heated at 140° C. in a sealed tube for 5 h. Flash chromatography (20/1 methylene chloride/methanol) afforded 1-ethyl-6-[4-(2-fluoro-phenyl)-piperazin-1-yl]-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (18 mg, 65%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.28 Hz, 3H) 3.1 (d, J=4.77 Hz, 4H) 3.2 (d, J=4.77 Hz, 4H) 4.0 (q, J=7.19 Hz, 2H) 5.8 (s, 1H) 6.3 (d, J=3.01 Hz, 1H) 6.9 (d, J=3.01 Hz, 1H) 7.1-7.2 (m, 3H) 10.6 (s, 1H). LC-MS calcd. for C19H22FN4O [(M+H)+] 341, obsd. 341.1.

Sources & evidence

ORD record
ord-18ca75c87f6c4ceb8131b5981bde3357
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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