Toluene → (1S)-1-Benzyl-2-(dimethylamino) Ethylamine

HRID 1879466Notes

Reaction equation

HRID 1879466 reaction equation
[NH2:1][C@@H:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([N:5]([CH3:7])[CH3:6])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(C)C=CC=CC=1.CCOCC>O1CCCC1.C(OCC)(=O)C>[CH3:7][N:5]([CH3:6])[CH2:3][C@@H:2]([NH2:1])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 11008771(S)-2-amino-N,N-dimethyl-3-phenylpropanamideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 11251722(1S)-1-Benzyl-2-(dimethylamino) EthylamineYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-amino-N,N-dimethyl-3-phenyl-propionamide (1.0 g, 5.2 mmol) in tetrahydrofuran (10 mL) was added a solution of lithium aluminum hydride in tetrahydrofuran and toluene (3.5 M, 7.4 mL, 26 mmol) dropwise. The mixture was heated to reflux for 4 h after addition and then cooled. Ether (20 mL) was added. Ethyl acetate was added dropwise until all the lithium aluminum hydride was consumed. Sodium hydroxide (1M, 20 mL) was added and the mixture was stirred for 30 min. The mixture was extracted three times with ether. The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated to give (S)—N1,N1-dimethyl-3-phenyl-propane-1,2-diamine (0.60 g, 65%)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. additionafter addition
  4. temperaturecooled
  5. customwas consumed
  6. additionSodium hydroxide (1M, 20 mL) was added
  7. extractionThe mixture was extracted three times with ether
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-36d5ee014ca64321aa6d9466f68f8a8c
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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