Water → N-Propyl-N-(tetrahydrofuran-3-yl)amine

HRID 650877

Reaction equation

HRID 650877 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=O)[CH2:14][CH3:15])[CH2:8]1.O.[OH-].[Na+]>C1COCC1>[CH2:13]([NH:12][CH:9]1[CH2:10][CH2:11][O:7][CH2:8]1)[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 21709920N-(Tetrahydrofuran-3-yl)propionamide

Product 1

HCID 21709909N-Propyl-N-(tetrahydrofuran-3-yl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 21.7 g (0.57 mol) of lithium aluminum hydride in 500 ml of THF was admixed dropwise with a solution of 81 g (0.57 mol) of N-(tetrahydrofuran-3-yl)propionamide, and the solution was heated at reflux for 2 h. Excess lithium aluminum hydride was hydrolyzed by dropwise addition of 16 ml of water, 50 ml of 10% strength aqueous sodium hydroxide solution and another 45 ml of water. The white suspension was heated at reflux for one hour, causing the insoluble components to aggregate to a coarse white precipitate. The mixture was filtered off from the precipitate, the precipitate was thoroughly rinsed with ether and the combined filtrates were distilled. B.p. 64° C. (12 mm), yield 41 g. 1H NMR (270 MHz, in CDCl3): δ=0.92 (t, 3H), 1.15 (s, 1H), 1.50 (sext., 2H), 1.70 (m, 1H), 2.10 (m, 1H), 2.55 (m, 2H), 3.38 (m, 1H), 3.56 (dd, 1H), 3.70-3.96 (m, 3H).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2 h
  3. temperatureThe white suspension was heated
  4. temperatureat reflux for one hour
  5. filtrationThe mixture was filtered off from the precipitate
  6. washthe precipitate was thoroughly rinsed with ether
  7. distillationthe combined filtrates were distilled

Sources & evidence

ORD record
ord-b88dadd5ce9e4356872d5cee917505c2
Source dataset
uspto-grants-2001_08
Patent number
US06277790B1

Linked notes

Loading…