Ethyl Acetate → (1S)-1-Benzyl-2-(dimethylamino) Ethylamine

HRID 1841620Notes

Reaction equation

HRID 1841620 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C@@H:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]([N:11]([CH3:13])[CH3:12])=O.C(OCC)(=O)C.[OH-].[Na+]>CCOCC.O1CCCC1>[CH2:14]([C@H:8]([NH2:7])[CH2:9][N:11]([CH3:13])[CH3:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 11008771(S)-2-amino-N,N-dimethyl-3-phenylpropanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11251722(1S)-1-Benzyl-2-(dimethylamino) EthylamineYield 75.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (759 mg) was suspended in anhydrous ether (20 ml) with ice cooling in the nitrogen gas atmosphere and then a solution of (2S)-2-amino-N1,N1-dimethyl-3-phenylpropionamide (1.92 g) in anhydrous tetrahydrofuran (10 ml) was dropwise added to the resulting suspension. This mixture was stirred at room temperature for 1.5 hour. Ethyl acetate was gradually and dropwise added to the reaction liquid till the latter did not undergo foaming any more, with ice cooling. Then a 2N aqueous sodium hydroxide solution was added to the reaction liquid and the resulting mixture was extracted with chloroform. The organic phase thus obtained was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to give the title compound (Reference Compound 1-1, 1.35 g).

Workup

  1. additiondropwise added to the reaction liquid till the latter
  2. extractionthe resulting mixture was extracted with chloroform
  3. customThe organic phase thus obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily product was purified through the silica gel column chromatography

Sources & evidence

ORD record
ord-d2f51e725f8f444e99e9d639d1ca2319
Source dataset
uspto-grants-2004_01
Patent number
US06683200B2

Reaction notes

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