Triethylamine → 1-(4-Ethylpiperidin-1-yl)-3-(4-methoxyphenyl)isoquinolinehydrochloride

HRID 1006955

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1.[CH2:20]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH3:21].C(N(CC)CC)C>CN(C)C=O>[ClH:1].[CH2:20]([CH:22]1[CH2:27][CH2:26][N:25]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[N:3]=2)[CH2:24][CH2:23]1)[CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

1-Chloro-3-(4-methoxyphenyl)isoquinoline (405 mg) and 4-ethylpiperidine (168 mg) were dissolved in N,N-dimethylformamide (5 ml), followed by the addition of triethylamine (251 ml), and the mixture was stirred at 80° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system). Then the resulting product was converted into a hydrochloride in a conventional manner, and then recrystallized from ethanol/isopropyl ether, to give the hydrochloride of the title compound as a colorless crystals (87 mg, yield; 13%).

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
washThe resulting organic layer was washed with water
dry with materialdried (over MgSO4)
customevaporated
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)
customrecrystallized from ethanol/isopropyl ether

Sources & evidence

ORD record: ord-c2af1ab155824703bebf4cabb2f0d6e2
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790844B2

Linked notes

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