Diisopropylethylamine → 1-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-4-methyl-piperidine-4-carboxylic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Ethyl 4-methylpiperidine-4-carboxylate	HCID 19361805	—
Reactant	3-Benzyl-6-chloro-4,5-dimethylpyridazine	HCID 59191487	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	1-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-4-methyl-piperidine-4-carboxylic acid ethyl ester	HCID 67176533	41%

Reaction Conditions

Temperature	210 °C

Reaction Steps

To a solution of 3-benzyl-6-chloro-4,5-dimethyl-pyridazine (1.0 g, 4.3 mmol) in NMP (10 mL) is added 4-methyl-piperidine-4-carboxylic acid ethyl ester (2.0 g, 8.6 mmol) and DIPEA (3.7 mL, 21.6 mmol). The mixture is heated in microwave at 210° C. for 1.5 h. The mixture is concentrated at 80° C. by rotovaporation. The crude product is purified by HPLC (CH3CN/H2O: 22% 45% with 0.1% TFA) to give 1-(6-benzyl-4,5-dimethyl-pyridazin-3-yl)-4-methyl-piperidine-4-carboxylic acid ethyl ester (0.64 g, 41%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09409871B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-0a8a2bf4bb6a4bb8afd801b58bd6e79e
Source note	uspto-grants-2016_08