Water → HCID 54235050, compound

HRID 1381909Notes

Reaction equation

HRID 1381909 reaction equation
C([N:3]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:4]([CH3:17])[CH2:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O1CC[CH2:36][CH2:35]1>>[CH2:35]([CH:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:5][CH:4]([NH:3][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:17])[CH3:36]

Participants

6

Reactant 5

HCID 962Water2×HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21275375HCID 21275375, compound

Product 1

HCID 54235050HCID 54235050, compound

Procedure

Dissolve 3.0 g (9 mmol) of 3-[ethyl(heptyl)amino]-N-(2-phenylethyl)butanamide in 50 mL of anhydrous tetrahydrofuran. Add this solution dropwise to a suspension of 0.68 g (18 mmol) of lithium aluminum hydride in 20 mL of anhydrous tetrahydrofuran under a nitrogen atmosphere. After the addition is complete heat the reaction mixture to reflux. Follow the progress of the reaction by thin layer chromatography on silica gel. At the completion of the reaction add successively dropwise 0.7 mL of water, 0.7 mL of 15% aqueous sodium hydroxide solution and 2.1 mL of water. Filter the resulting solids and wash with 20 mL of tetrahydrofuran. Evaporate the solvent in vacuo and dissolve the residue in 100 mL of methylene chloride. Wash the methylene chloride solution with 20 mL of water and 20 mL of saturated sodium chloride solution then dry over anhydrous sodium sulfate. Remove the drying agent and evaporate the solvent to obtain the title compound.

Workup

  1. additionAdd this solution
  2. additionAfter the addition
  3. temperatureis complete heat the reaction mixture
  4. temperatureto reflux
  5. customthe progress of the reaction by thin layer chromatography on silica gel
  6. filtrationFilter the resulting solids
  7. washwash with 20 mL of tetrahydrofuran
  8. customEvaporate the solvent in vacuo
  9. dissolutiondissolve the residue in 100 mL of methylene chloride
  10. washWash the methylene chloride solution with 20 mL of water and 20 mL of saturated sodium chloride solution
  11. dry with materialthen dry over anhydrous sodium sulfate
  12. customRemove the drying agent
  13. customevaporate the solvent

Sources & evidence

ORD record
ord-8ba4c3999ef0401babdfffc4b56aa125
Source dataset
uspto-grants-1989_02
Patent number
US04804662

Reaction notes

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