Réaction #84054

Équation de réaction

hydrochloric acid

1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride

thionyl chloride

triethylamine

8-nitro-2-naphthylamine

thionyl chloride

→

title compound

2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl)acetamide hydrochloride

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreAfter reaction overnight and purification by preparative HPLC
2. 2
   Concentrationconcentrated in vacuo
3. 3
   AutreRecrystallization
4. 4
   Séchageof the residue from isopropanol and drying under high vacuum

Mode opératoire

200 mg (0.97 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride are heated under reflux in 2 ml (27.42 mol) of thionyl chloride for 2 h. The mixture is then freed of excess thionyl chloride in vacuo, and the residue is taken up in 4 ml of DMF. 0.54 ml (3.89 mmol) of triethylamine, 59.4 mg (0.4 mmol) of DMAP and 183.0 mg (0.97 mmol) of 8-nitro-2-naphthylamine are added to this solution. After reaction overnight and purification by preparative HPLC, the resulting product fractions are mixed with 1 M hydrochloric acid and concentrated in vacuo. Recrystallization, of the residue from isopropanol and drying under high vacuum result in 59 mg (15% of theory) of the title compound.

Source