Sodium hydride → (1-(2-(isopropoxy)ethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

Participants

Role	Name	HCID	Charge
Reactant	Sodium hydride	HCID 24758	—
Reactant	2-Isopropoxyethyl Methanesulfonate	HCID 18465045	—
Reactant	tert-Butyl 4-((1H-benzo[d]imidazol-2-yl)amino)piperidine-1-carboxylate	HCID 22036999	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(1-(2-(isopropoxy)ethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine	HCID 22009477	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

Combine (1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (2.76 g, 8.72 mmol), and sodium hydride (0.38 g, 9.5 mmol) in dimethylformamide (30 mL). After 30 minutes, add 2-(isopropoxy)ethyl mesylate (0.51 g, 5.5 mmol). Heat to 80° C. After 2.5 hours, cool the reaction mixture to ambient temperature and partition between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the organic layer with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give (1-(2-(isopropoxy)ethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine: Rf=0.73 (silica gel, dichloromethane/methanol/concentrated ammonium hydroxide, 90/10/0.1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06211199B1
Source dataset	uspto-grants-2001_04
ORD ID	ord-f9eb27cac30d489b8aaebfd70ba6de90
Source note	uspto-grants-2001_04