1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → 4-[3-(4,5-dihydro-1H-imidazol-2-yl)propyl]piperidine

Participants

Role	Name	HCID	Charge
Reactant	1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)	HCID 225030	—
Reactant	4-(3-Cyanopropyl)-1-piperidinecarboxaldehyde	HCID 20239759	—
Reactant	HCID 178418582	HCID 178418582	—
Solvent	Ethanol	HCID 702	—
Product	4-[3-(4,5-dihydro-1H-imidazol-2-yl)propyl]piperidine	HCID 13281189	72.5%

Reaction Conditions

Temperature	200 °C

Reaction Steps

To 4-(3-cyanopropyl)-1-piperidinecarboxaldehyde (10 g, 0.055 M), there was added ethylenediamine p-toluenesulfonate (30 g, 0.129 M) and the mixture was heated at 200° C. for 41/2 hours. The reaction mixture was dissolved in ethanol (100 ml), basified with MeONa (0.26 M), filtered and stripped to dryness. The residue was distilled at 170° C., 0.025 mmHg to give 4-[3-(4,5-dihydro-1H-imidazol-2-yl)propyl]piperidine (7.86 g, 72% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04431653
Source dataset	uspto-grants-1984_02
ORD ID	ord-58b819737fa54f8f82ae7a4818909f97
Source note	uspto-grants-1984_02