Phenethylamine → 2-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic Acid Benzyl Ester

Participants

Role	Name	HCID	Charge
Reactant	Phenethylamine	HCID 1001	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	6-(2,2-Dimethoxy-ethyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester	HCID 54351909	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic Acid Benzyl Ester	HCID 54510493	86%

Reaction Steps

6-(2,2-Dimethoxy-ethyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester (Compound 238, 0.335 g, 0.96 mmol) and phenethyl amine (0.14 g, 1.15 mmol) were dissolved CH2Cl2 (20 mL). HOBt (0.156 g, 1.15 mmol) was added followed by EDC.HCl (0.221 g, 1.15 mmol). The reaction was stirred at room temperature for 18 hours. Saturated NaHCO3 solution (25 mL) was added and then extracted with CHCl3 (2×50 mL). The combined organic layers were dried over Na2SO4, and then concentrated. Flash chromatographic purification of the residue (1:1 EtOAc/hexanes) gave Compound 239 (0.374 g, 86%). Rf=0.47 (1:1 EtOAC/hexanes).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06630472B1
Source dataset	uspto-grants-2003_10
ORD ID	ord-dca6f6e4208b4f12b57989d2c6f8a457
Source note	uspto-grants-2003_10