Dimethylformamide → (1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Ethyl bromoacetate	HCID 7748	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	tert-Butyl 4-((1H-benzo[d]imidazol-2-yl)amino)piperidine-1-carboxylate	HCID 22036999	—
Solvent	Dichloromethane methanol	HCID 21226129	—
Product	(1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine	HCID 22009058	—

Reaction Steps

Combine (1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (0.5 g, 1.58 mmol) and dimethylformamide (10 mL). Add portionwise, sodium hydride (0.08 g, 60% in oil, 1.66 mmol). After 30 minutes, add ethyl bromoacetate (0.277 g, 1.66 mmol). After 12 hours, quench by the addition of water and extract the quenched reaction mixture with dichloromethane. Separate the layers and extract the organic layer with five times with water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane to give (1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06211199B1
Source dataset	uspto-grants-2001_04
ORD ID	ord-f8b7fed7d0ed499c9efcd99fc256ff8d
Source note	uspto-grants-2001_04