Dimethyl Sulfoxide → 4-[1-[2-(Benzyl-methyl-amino)-ethyl]-4-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Dimethyl Sulfoxide	HCID 679	—
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	N-(2-Chloroethyl)-N-methylbenzylamine hydrochloride	HCID 12822620	—
Reactant	HCID 178451793	HCID 178451793	—
Solvent	Water methylene chloride	HCID 21908982	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	4-[1-[2-(Benzyl-methyl-amino)-ethyl]-4-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester	HCID 67264856	79%

Reaction Steps

Add powdered KOH (283 mg; 5.05 mmol) and 4-[4-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (2.02 mmol; 768 mg) to DMSO (6 mL). Then add benzyl-(2-chloro-ethyl)-methylamine hydrochloride (2.22 mmol; 0.49 mL) in one portion and heat to 40° C. for 18 h. Cool, dilute with DCM/water, add brine and separate layers. Wash the organic phase with water, brine, dry over MgSO4, filter and evaporate. Purify on 120 g silica gel with 1% MeOH/DCM to provide the title compound (840.5 mg; 79%). MS (ES): m/z=527 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08148387B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-45901961ef0b4b54abc2b9607fa1e5b2
Source note	uspto-grants-2012_04