Sodium Hydroxide → (R)-3-(2-methoxyethylamino)-1-phenylmethylpiperidine

HRID 1615

Reaction equation

HRID 1615 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][C:10]([NH:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14]1)=O.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)(=O)C.O1CCCC1>[CH3:7][O:8][CH2:9][CH2:10][NH:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydride2×HCID 51728477(R)-3-(methoxyacetylamino)-1-phenylmethylpiperidine

Product 1

HCID 53883265(R)-3-(2-methoxyethylamino)-1-phenylmethylpiperidineYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

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.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. temperaturethe mixture was refluxed for 3 hours
  3. stirringThe reaction mixture was stirred
  4. temperatureunder cooling with ice
  5. filtrationit was filtered with celite
  6. distillationThe filtrate was distilled off under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by column chromatography (alumina, ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-e6ecab20c64a406a8e7634f4425b54c1
Source dataset
uspto-grants-1998_03
Patent number
US05726188

Linked notes

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