Reaktion #88072

Reaktionsgleichung

tert-Butyl 4-((4-chlorophenethyl)(3-cyanobenzyl)amino)piperidine-1-carboxylate

sodium azide

triethylamine hydrochloride

→

tert-Butyl 4-((3-(1H-tetrazol-5-yl)benzyl)(4-chlorophenethyl)amino)piperidine-1-carboxylate

Ausbeute 60.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe heterogeneous mixture was refluxed for 3 days after which time the starting material
2. 2
   Filtrationwere filtered off
3. 3
   SonstigeThe crude product was purified by silica gel chromatography (yield 60%)

Vorschrift

tert-Butyl 4-((4-chlorophenethyl)(3-cyanobenzyl)amino)piperidine-1-carboxylate obtained in Step 1 was dissolved in toluene (5 mL/mmol) and sodium azide (3 equiv) and triethylamine hydrochloride (0.1 equiv) were added to this solution. The heterogeneous mixture was refluxed for 3 days after which time the starting material could no longer be detected. After cooling down to ambient temperature the solids were filtered off and the solvent was stripped off in vacuo. The crude product was purified by silica gel chromatography (yield 60%).

Quelle