Potassium Carbonate → 1-[2-(4-Iodophenoxy)ethyl]-4-methylpiperidin-4-ol

HRID 734783Notes

Reaction equation

HRID 734783 reaction equation
C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=1)(=O)=O.[CH3:22][C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(Cl)Cl.CO>[I:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][N:26]2[CH2:27][CH2:28][C:23]([CH3:22])([OH:29])[CH2:24][CH2:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 156491744-Methylpiperidin-4-olHCID 866011312-(4-Iodophenoxy)ethyl methanesulfonate

Product 1

HCID 578453271-[2-(4-Iodophenoxy)ethyl]-4-methylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The product was obtained analogously to Example 1.1g (3 hours at 70° C., potassium carbonate as base) from 4.79 g (14.0 mmol) of 2-(4-iodophenoxy)ethyl methanesulfonate and 1.94 g (16.8 mmol) of 4-methylpiperidin-4-ol. Yield: 3.40 g (67% of theoretical); C14H20INO2 (M=361.219); calc.: molpeak (M+H)+: 362; found: molpeak (M+H)+: 362; Rf value: 0.20 (silica gel, DCM/MeOH 9:1).

Sources & evidence

ORD record
ord-c40b3c1d88554906aaba90ebb0f7e914
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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