Reaction #1711

Reaction equation

lithium aluminum hydride

magnesium sulfate

(R)-3-(2-methoxyacetylamino)-1-phenylmethylpiperidine

sodium hydroxide

lithium aluminum hydride

→

title compound

Yield 72.0%

(R)-3-(2-methoxyethylamino)-1-phenylmethylpiperidine

Yield 72.0%

Solvents

tetrahydrofuran

ethyl acetate

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was refluxed for 3 hours
2. 2
   Temperaturethe mixture was refluxed for 3 hours
3. 3
   workup.STIRRINGThe reaction mixture was stirred
4. 4
   Temperatureunder cooling with ice
5. 5
   Filtrationit was filtered with celite
6. 6
   workup.DISTILLATIONThe filtrate was distilled off under reduced pressure
7. 7
   Otherthe residue thus obtained
8. 8
   Otherwas purified by column chromatography (alumina, ethyl acetate:n-hexane=1:2)

Procedure

To a 50 ml anhydrous tetrahydrofuran suspension of 0.87 g (2.0 eg.) of lithium aluminum hydride in a 300 ml round-bottomed flask was added dropwise a 20 ml anhydrous tetrahydrofuran solution of 3.00 g (11.4 mmol) of (R)-3-(2-methoxyacetylamino)-1-phenylmethylpiperidine. After stirred for 1 hour at room temperature, the reaction mixture was refluxed for 3 hours. Further, 0.87 g (2.0 eg.) of lithium aluminum hydride were added and the mixture was refluxed for 3 hours. The reaction mixture was stirred under cooling with ice and, after added 180 ml of ethyl acetate and a 10 ml aqueous solution of sodium hydroxide (1.82 g, 4.0 eg.) in turn to this and stirred for 30 minutes, anhydrous magnesium sulfate was added and it was filtered with celite. The filtrate was distilled off under reduced pressure and the residue thus obtained was purified by column chromatography (alumina, ethyl acetate:n-hexane=1:2) to obtain 2.03 g (yield 72 %) of title compound as a brown oil.

Source