4-Methylmorpholine → 1-tert-Butoxycarbonyl-4-[4-(4-pyridyl)benzoyl]piperazine

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	tert-Butyl piperazine-1-carboxylate	HCID 143452	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	4-(Pyridin-4-yl)benzoic acid hydrochloride	HCID 57432607	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-tert-Butoxycarbonyl-4-[4-(4-pyridyl)benzoyl]piperazine	HCID 22709443	—

Reaction Steps

In N,N-dimethylformamide (40 ml), 4-(4-pyridyl)benzoic acid hydrochloride (654 mg) and tert-butyl 1-piperazinecarboxylate (569 mg) were suspended. To the resulting suspension, 1-hydroxybenzotriazole (374 mg) and N-methylmorpholine (336 μl) were added. The resulting mixture was ice cooled, followed by the addition of 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (796 mg). After stirring at room temperature for 7 hours, the solvent was distilled off. The residue was purified by chromatography on a silica gel column (2% methanol—dichloromethane), followed by washing with hexane, whereby the title compound (905 mg, 89%) was obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06747023B1
Source dataset	uspto-grants-2004_06
ORD ID	ord-b9d70e5f9668448d85d5a0ed3dd1d370
Source note	uspto-grants-2004_06