Reaction #1583881

Reaction equation

3-methylpyrrolidin-3-ol hydrochloride

3-methylpyrrolidin-3-ol hydrochloride

potassium carbonate

3-bromopropylbenzene

→

3-methyl-1-(3-phenylpropyl)pyrrolidin-3-ol

Yield 70.4%

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   Otherwas synthesized
2. 2
   OtherTo a 100 mL reaction flask
3. 3
   OtherAfter the completion of reaction
4. 4
   Otherthe resulting mixture was evaporated under reduced pressure
5. 5
   Otherto remove acetonitrile
6. 6
   workup.ADDITIONTo the residue was added a mixed solution of dichloromethane and water
7. 7
   Extractionfor extraction
8. 8
   DryingThe organic phase was dried over anhydrous sodium sulfate
9. 9
   Otherevaporated
10. 10
    Otherto remove the solvent
11. 11
    Otherto produce a crude product
12. 12
    OtherThe crude product was purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=10:1 (volumetric ratio))

Procedure

According to Example 15, 3-methylpyrrolidin-3-ol hydrochloride was synthesized. To a 100 mL reaction flask were added 3-methylpyrrolidin-3-ol hydrochloride (1 g, 7.2 mmol), anhydrous potassium carbonate (2.5 g, 18 mmol) and acetonitrile (15 mL). To the resulting mixture was slowly added a solution of 3-bromopropylbenzene (1.29 g, 6.48 mmol) in acetonitrile dropwisely at 85° C. The reaction was conducted for 12 hours. After the completion of reaction monitored by TLC, the resulting mixture was evaporated under reduced pressure to remove acetonitrile. To the residue was added a mixed solution of dichloromethane and water for extraction. The organic phase was dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce a crude product. The crude product was purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=10:1 (volumetric ratio)) to produce 3-methyl-1-(3-phenylpropyl)pyrrolidin-3-ol (1 g) in a yield of 70.4%.

Source