Benzylamine → HCID 25181839, compound

Participants

Role	Name	HCID	Charge
Reactant	Benzylamine	HCID 7504	—
Reactant	Diisopropylamine	HCID 7912	—
Reactant	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Reactant	6-(4-Methylpiperazin-1-yl)pyridine-3-carboxylic acid	HCID 14987926	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 25181839	HCID 25181839	—

Reaction Steps

A suspension of 6-(4-methyl-piperazin-1-yl)-nicotinic acid (200 mg) in DMF (2 ml) was treated under an argon atmosphere with diisopropylamine (0.50 ml), benzylamine (0.12 ml) and BOP (600 mg). The reaction mixture was stirred at r.t. overnight, then diluted with water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 9:1) to give N-benzyl-6-(4-methyl-piperazin-1-yl)-nicotinamide (120 mg) as off-white solid. MS (ISP): 311.3 ([M+H]+)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08008305B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-65b01385210f4132a5be97f651c11f1b
Source note	uspto-grants-2011_08