Reaction #58206

Reaction equation

N-[8-(naphthalen-2-ylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]acetamide

hydrochloric acid

sodium hydroxide

→

oily product

Yield 94.0%

N-[8-(naphthalen-2-ylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]amine

Yield 94.0%

Conditions

Workup

1. 1
   TemperatureThe mixture is refluxed for 4 hours
2. 2
   Temperaturecooled in an ice bath
3. 3
   Extractionextracted three times with ethyl acetate
4. 4
   WashThe combined extracts are washed with water and with brine
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Otherevaporated under reduced pressure

Procedure

4 g (12.9 mmol) of N-[8-(naphthalen-2-ylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]acetamide are poured into 13 mL of 5N hydrochloric acid. The mixture is refluxed for 4 hours and then cooled in an ice bath, basified with 35% sodium hydroxide and extracted three times with ethyl acetate. The combined extracts are washed with water and with brine, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. 3.2 g of oily product are obtained (94% yield).

Source