Potassium Carbonate → 2-methyl-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine

HRID 657670Notes

Reaction equation

HRID 657670 reaction equation
Br.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl.CS(O[CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][CH2:34][C@H:33]([CH3:37])[CH2:32]1)(=O)=O>CN(C)C=O>[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][C@H:33]([CH3:37])[CH2:32]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86629975(3S)-1-(3-methane-sulfonyloxypropyl)-3-methylpiperidine hydrochlorideHCID 1363360532-Methyl-4-(4-hydroxyphenyl)pyridine hydrobromide

Product 1

HCID 159409262-methyl-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A Following the procedure described in example 56A, but starting from 2-methyl-4-(4-hydroxyphenyl)pyridine hydrobromide (130 m g), potassium carbonate (415 g), (3S)-1-(3-methanesulfonyloxypropyl)-3-methylpiperidine hydrochloride (170 mg) and N,N-dimethylformamide (5 mL) gives 82 mg of 2-methyl-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine, dioxalate as a pale yellow powder melting at 97° C.

Sources & evidence

ORD record
ord-e0088885c2264b5d9e5fcb27b8643c4c
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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