1-(3-fluoro-4-methylphenyl)piperazine → HCID 18523254, compound

HRID 413040Notes

Reaction equation

[Cl:1][C:2]1[C:22](F)=[CH:21][C:5]2[C:6]3[C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][N:10]([CH3:14])[C:11]=3[CH:12]=[N:13][C:4]=2[C:3]=1[F:24].[F:25][C:26]1[CH:27]=[C:28]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:29]=[CH:30][C:31]=1[CH3:32]>CS(C)=O>[Cl:1][C:2]1[C:22]([N:36]2[CH2:35][CH2:34][N:33]([C:28]3[CH:29]=[CH:30][C:31]([CH3:32])=[C:26]([F:25])[CH:27]=3)[CH2:38][CH2:37]2)=[CH:21][C:5]2[C:6]3[C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][N:10]([CH3:14])[C:11]=3[CH:12]=[N:13][C:4]=2[C:3]=1[F:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred suspension of 1 g of ethyl 8-chloro-7,9-difluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate and 1.2 g of 1-(3-fluoro-4-methylphenyl)piperazine in 15 cm3 of dimethyl sulphoxide was heated to a temperature in the region of 80° C. After 20 hours, 0.6 g of 1-(3-fluoro-4-methylphenyl)piperazine was added and the heating was continued for an additional 8 hours. After 28 hours, the reaction mixture was cooled and then filtered. The precipitate was washed twice with 10 cm3 of water, twice with 5 cm3 of ethanol, and twice with 5 cm3 of diisopropyl ether. 0.64 g of ethyl 8-chloro-7-fluoro-9-[4-(3-fluoro-4-methylphenyl)piperazin-1-yl]-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate was obtained in the form of a greenish-yellow solid, which melted at 350° C. with decomposition.

Workup

waitthe heating was continued for an additional 8 hours
waitAfter 28 hours
temperaturethe reaction mixture was cooled
filtrationfiltered
washThe precipitate was washed twice with 10 cm3 of water, twice with 5 cm3 of ethanol

Sources & evidence

ORD record: ord-7d192d0cf96d47d38f2c320cc1c12b57
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566362B2

Reaction notes

Loading…