Reaction #67604

Reaction equation

Bromomethylcyclobutane

noroxymorphone

Noroxymorphone

potassium carbonate

potassium iodide

bromomethylcyclobutane

→

N-(cyclobutylmethyl)-noroxymorphone

Yield 73.2%

Solvents

dimethyl acetamide

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred for an additional 7 days
2. 2
   Otherwas consumed
3. 3
   workup.ADDITIONDistilled water (50 mL) was added
4. 4
   workup.STIRRINGstirred at room temperature for 6 hours
5. 5
   OtherAn off-white precipitate formed
6. 6
   Otherwhich was removed by filtration
7. 7
   WashThe solid was washed with distilled water (25 mL)
8. 8
   workup.WAITslurried for 24 hours in acetonitrile (25 mL)
9. 9
   FiltrationFiltration
10. 10
    Washwashing the solid with acetonitrile (10 mL)
11. 11
    Otherdrying at room temperature under vacuum for 24 hours

Procedure

Noroxymorphone (1.59 g, 5.5 mmol), potassium carbonate (0.61 g, 6.1 mmol), potassium iodide (0.46 g, 2.8 mmol), and dimethyl acetamide (10 mL) were added into a round bottom flask. Bromomethylcyclobutane (0.82 g, 5.5 mmol, 0.62 mL) was added. The reaction was stirred for 7 days at room temperature. At that time, bromomethylcyclobutane (0.82 g, 5.5 mmol, 0.62 mL) was added. The reaction was stirred for an additional 7 days. HPLC analysis indicated that the noroxymorphone was consumed. Distilled water (50 mL) was added and stirred at room temperature for 6 hours. An off-white precipitate formed, which was removed by filtration. The solid was washed with distilled water (25 mL), then slurried for 24 hours in acetonitrile (25 mL). Filtration, washing the solid with acetonitrile (10 mL), and drying at room temperature under vacuum for 24 hours yielded N-(cyclobutylmethyl)-noroxymorphone (1.43 g, 73% yield) as a tan solid.

Source