Acetic Acid → 6-[4-(4-Fluorphenyl)piperazin-1-yl]-1,3,5-triazine-2,4(1H,3H)-dione

HRID 1477576Notes

Reaction equation

[C:1]([OH:4])(=O)C.Cl[C:6]1[N:11]=C(Cl)[N:9]=[C:8]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[N:7]=1.C([O-])(=[O:28])C.[Na+]>O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[NH:7][C:6](=[O:28])[NH:11][C:1](=[O:4])[N:9]=3)[CH2:14][CH2:15]2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

An acetic acid solution of 2,4-dichloro-6-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazine (2.40 g, 7.31 mmol) synthesized in Reference Synthesis Example 1 and sodium acetate (1.80 g) was stirred at 80° C. for 8 hours. After completion of the reaction, the reaction solution was poured into water and the obtained solid was collected by filtration. Extraction with ethyl acetate was performed from the filtrate and the resultant ethyl acetate phase was concentrated under reduced pressure. The residue and the solid collected by filtration were combined and the combination was suspended into ethyl acetate, collected by filtration, washed with ethyl acetate, and dried under reduced pressure to obtain the title compound (1.82 g, yield 86%).

Workup

customAfter completion of the reaction
filtrationthe obtained solid was collected by filtration
extractionExtraction with ethyl acetate
concentrationthe resultant ethyl acetate phase was concentrated under reduced pressure
filtrationThe residue and the solid collected by filtration
filtrationcollected by filtration
washwashed with ethyl acetate
customdried under reduced pressure

Sources & evidence

ORD record: ord-88a03e277fc74d18b707b7c77aa4a100
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403798B2

Reaction notes

Loading…