Piperidine → Ether hydrochloride

Participants

Role	Name	HCID	Charge
Reactant	Piperidine	HCID 8082	—
Reactant	Triethylamine	HCID 8471	—
Reactant	1,1'-Carbonyldiimidazole	HCID 68263	—
Reactant	2,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-8-amino-1H-1,4-benzodiazepine, dihydrochloride	HCID 178478650	—
Solvent	Chloroform	HCID 6212	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	Ether hydrochloride	HCID 10953452	—
Product	N-[2,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepin-8-yl]-1-piperidinecarboxamide, dihydrochloride	HCID 178478887	—

Reaction Steps

Carbonyidiimidazole (0.045 g, 0.137 mmol), was added to a solution of Example 26 (0.050 g, 0.125 mmol), and triethylamine (0.038 mL, 0.275 mmol) in dry methylene chloride (1 mL) at rt under argon. After stirring for 2 hr, piperidine (0.013 mL, 0.13 mmol) was added. After stirring for 15 hr, the reaction was diluted with NaHCO3 and CHCl3. The organic layer was washed with NaHCO3, water, and brine (1×3 mL each), dried over MgSO4, filtered and concentrated. The product was purified by reverse phase HPLC with a gradient of 40-90% aquous methanol with 0.1% TFA and the HCl salt was formed by treatment with 1M HCl/ether to afford Example 247 (0.006 g, 10%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06011029
Source dataset	uspto-grants-2000_01
ORD ID	ord-2139a2414ebb49b38fba161beabdfbc8
Source note	uspto-grants-2000_01