Phenol → HCID 71472628, compound

HRID 1506747Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](Cl)=[C:11]1[C:6]([CH:7]=[CH:8][C:9]([O:17][CH3:18])=[CH:10]1)=[N:5]2.C1(O)C=CC=CC=1.[CH2:26]([N:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)[CH3:27]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:34][CH:31]1[CH2:32][CH2:33][N:28]([CH2:26][CH3:27])[CH2:29][CH2:30]1)=[C:11]1[C:6]([CH:7]=[CH:8][C:9]([O:17][CH3:18])=[CH:10]1)=[N:5]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6,9-dichloro-2-methoxyacridine (100 mg, 0.36 mmol) and phenol (approximately 1.5 g) was heated to 100° C. under nitrogen atmosphere and stirred for 1 hour. 1-Ethylpiperidin-4-amine (92 mg, 0.72 mmol) was added to the mixture. The reaction was stirred at 100° C. for 5 hours, cooled to 20-25° C., and diluted with dichloromethane. The mixture was washed twice with sodium hydroxide solution (1 N) and twice with ammonium chloride solution. The phases were separated, and the organic layer was dried and concentrated. The residue was purified by Biotage column chromatography using triethylamine (5%) and methanol (5 to 15%) in dichloromethane to give the title compound; MS (Found: M+1=370).

Workup

stirringThe reaction was stirred at 100° C. for 5 hours
temperaturecooled to 20-25° C.
washThe mixture was washed twice with sodium hydroxide solution (1 N) and twice with ammonium chloride solution
customThe phases were separated
customthe organic layer was dried
concentrationconcentrated
customThe residue was purified by Biotage column chromatography

Sources & evidence

ORD record: ord-c02a49d7ae2d45c29cbcf18a4d975db6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221760B2

Reaction notes

Loading…