1,3,5-Trimethoxybenzene → 1,2,3,6-Tetrahydro-1-(4-methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)pyridine

HRID 1363380Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

Compound of example 117 (19.0 g, 92 mmol) was added to a solution of 1,3,5-trimethoxybenzene (21.8 g, 130 mmol) in glacial acetic acid (50 mL) at 25° C. HCl gas was bubbled through the reaction mixture for 1 h, slowly raising the temperature up to 90° C. Acetic acid was removed under reduced pressure and the semisolid residue was poured over crushed ice (300 g). The resulting solution was made basic using an aqueous 50% NaOH solution. The precipitated solid was filtered, washed with water and dried. The solid was added slowly to boiling methanol, stirred for fifteen minutes and filtered to remove traces of trimethoxybenzene and the filtrate was concentrated to get the title compound.

Workup

customHCl gas was bubbled through the reaction mixture for 1 h
customAcetic acid was removed under reduced pressure
additionthe semisolid residue was poured
customover crushed ice (300 g)
filtrationThe precipitated solid was filtered
washwashed with water
customdried
additionThe solid was added slowly
filtrationfiltered
customto remove traces of trimethoxybenzene
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-e1997ba950f64671b54fadd9d5b79e97
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884127B2

Reaction notes

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