Sodium hydride → (+/-)-1,1-dimethylethyl 4-[[1-[2-hydroxy-2-(6-methyl-2-pyridinyl)ethyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium hydride	HCID 24758	—
Reactant	2-Methyl-6-(oxiran-2-yl)pyridine	HCID 21928164	—
Reactant	tert-Butyl 4-((1H-benzo[d]imidazol-2-yl)amino)piperidine-1-carboxylate	HCID 22036999	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(+/-)-1,1-dimethylethyl 4-[[1-[2-hydroxy-2-(6-methyl-2-pyridinyl)ethyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate	HCID 22711809	38.8%

Reaction Conditions

Temperature	40 °C

Reaction Steps

Reaction under N2 flow. NaH 60% (0.02 mol) was added to a mixture of 1.1-dimethylethyl 4-(1H-benzimidazol-2-ylamino)-1-piperidinecarboxylate (0.02 mol) in N,N-di-methylformamide (100 ml). The mixture was stirred at 40° C. for 1 hour. 6-(Epoxyethyl)-2-picoline (0.02 mol) in a small amount of N,N-dimethylformamide was added. The mixture was stirred at 100° C. overnight. The solvent was evaporated. The residue was taken up in H2O and CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5 and 90/10). The pure fractions were collected and the solvent was evaporated, yielding 3.5 g of (±)-1,1-dimethylethyl 4-[[1-[2-hydroxy-2-(6-methyl-2-pyridinyl)ethyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate (interm. 16).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07528149B2
Source dataset	uspto-grants-2009_05
ORD ID	ord-e91e1030a0f04c70819a3ce1a65fe3d4
Source note	uspto-grants-2009_05