Sulfuric acid magnesium salt (1:1) → (S)-N-methyl-(2-phenylpent-4-enyl)amine

HRID 1584496Notes

Reaction equation

HRID 1584496 reaction equation
[CH3:1][NH:2][C:3](=O)[C@H:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:6]=[CH2:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:1][NH:2][CH2:3][C@H:4]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 86754359(S)-2-phenylpent-4-enoic acid, N-methyl amide

Product 1

HCID 53688463(S)-N-methyl-(2-phenylpent-4-enyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine (S)-2-phenylpent-4-enoic acid, N-methyl amide (1.35 g, 7.13 mmol) and tetrahydrofuran (20 mL). Cool in an ice bath, add a solution of lithium aluminum hydride (17 mL, 1.0 M in tetrahydrofuran, 17 mmol). After the addition is complete, heat the reaction mixture to reflux. After 24 hours, cool in an ice bath and carefully quench with water (0.6 mL), an aqueous 15% sodium hydroxide solution (0.6 mL) and then water (2 mL). Dilute the quenched reaction mixture with diethyl ether (50 mL), add MgSO4, and stir. After 2 hours, filter through celite and rinse the solids with dichloromethane. Dry the filtrate with MgSO4, and evaporate in vacuo to give (S)-N-methyl-(2-phenylpent-4-enyl)amine: Rf =0.51 (silica gel, 18/2/0.2 dichloromethane/methanol/concentrated aqueous ammonia).

Workup

  1. temperatureCool in an ice bath
  2. additionAfter the addition
  3. temperatureheat the reaction mixture
  4. temperatureto reflux
  5. temperaturecool in an ice bath
  6. customcarefully quench with water (0.6 mL)
  7. additionDilute
  8. customthe quenched reaction mixture with diethyl ether (50 mL)
  9. waitAfter 2 hours
  10. filtrationfilter through celite
  11. washrinse the solids with dichloromethane
  12. dry with materialDry the filtrate with MgSO4
  13. customevaporate in vacuo

Sources & evidence

ORD record
ord-cb7c6850e4944ec68736320140b76f60
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

Loading…