Dimethylformamide → (1-methyl-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Methyl iodide	HCID 6328	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	1-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl ester	HCID 3018455	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(1-methyl-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine	HCID 12891475	—

Reaction Steps

Combine (1H-benzimidazol-2-yl)(1-ethoxycarbonyl-piperidin-4-yl)amine (1.44 g, 5.0 mmol) and dimethylformamide (3 mL) and tetrahydrofuran (25 mL). Add sodium hydride (0.34 g, 60% in oil, 8.5 mmol). After 1 hour, add methyl iodide (1 mL). After 18 hours, evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give (1-methyl-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine: Rf=0.25 (silica gel, ethyl acetate).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06211199B1
Source dataset	uspto-grants-2001_04
ORD ID	ord-a33a733eff84422b92b74627be473a12
Source note	uspto-grants-2001_04