Phenol → 1-(6.7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3-methyl-2-(phenoxy)butan-1-one

HRID 1760047Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CN(C=O)C.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[CH2:23][N:22]([C:29](=[O:35])[CH:30](Br)[CH:31]([CH3:33])[CH3:32])[CH2:21][CH2:20]2>C(OCC)(=O)C.CCCCCC>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[CH2:23][N:22]([C:29](=[O:35])[CH:30]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:31]([CH3:33])[CH3:32])[CH2:21][CH2:20]2

Participants

Conditions

Temperature: 80 °C

Procedure

Phenol (50 μl, 0.569 mmol) and sodium hydride (60% in a mineral oil, 10 mg) were added to a DMF (2 ml) solution of 1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3-methyl-2-bromobutan-1-one (54 mg, 0.152 mmol) obtained in Reference example 16, and the mixture was stirred at 80° C. for 10 hours and cooled to room temperature. The reaction solution was diluted with ethyl acetate and hexane (1:1, 50 ml), washed with a 1 N aqueous sodium hydroxide solution (30 ml) and 1 N hydrochloric acid (30 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to preparative thin layer chromatography using ethyl acetate and hexane (1:1) as an eluent to obtain the captioned compound (30.7 mg, 55%) as a yellow oily substance.

Workup

customobtained in Reference example 16
temperaturecooled to room temperature
washwashed with a 1 N aqueous sodium hydroxide solution (30 ml) and 1 N hydrochloric acid (30 ml)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-79d22624e9c345c29d2201bc6225ef98
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838465B2

Reaction notes

Loading…