2-Methylpyridine → 2-[7-(2-Chloro-4-methoxyphenoxy)heptyl]pyridine

HRID 1289606Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])CCC.[Cl:13][C:14]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]SC1SCC(=O)N=1>O1CCCC1>[Cl:13][C:14]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Under a nitrogen atmosphere, add 152 mg. 2-picoline and 1.5 ml. tetrahydrofuran (THF) and cool to -28° C. Add 104 mg. n-butyl lithium and stir about 30 minutes at -78° C. Add 20 mg. of the iodide prepared in Examples 2 and 3 in 1 ml. THF. Stir 1 hour at -78° C., let warm to room temperature and stir about 15 hours. Work up with water and methylene chloride then wash with water and brine then.dry over sodium sulfate. Elute on a coarse silica column with methylene chloride then 50% ethylacetate/methylene chloride to obtain the title compound. Prepare the hydrochloride salt by reaction of the title compound with 0.1N HCl.

Workup

additionUnder a nitrogen atmosphere, add 152 mg
additionAdd 104 mg
additionAdd 20 mg
temperaturelet warm to room temperature
stirringstir about 15 hours
washWork up with water and methylene chloride then wash with water and brine then.dry over sodium sulfate
washElute on a coarse silica column with methylene chloride

Sources & evidence

ORD record: ord-a5ec1fd6d723483f9cce9776a3b104ea
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750532

Reaction notes

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