Tetrahydrofuran → 4-Butylbenzylamine

HRID 1731850Notes

Reaction equation

HRID 1731850 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=O)=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10].O1CCCC1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[CH2:7]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:17])=[CH:18][CH:19]=1)[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 62649Sodium sulfate decahydrateHCID 28014584-ButylbenzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 40298714-ButylbenzylamineYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 15 g of lithium aluminum hydride in 200 ml of anhydrous ethyl ether under argon was added, at room temperature, a solution of 32. 0 g of 4-butylbenzamide in 200 ml of freshly distilled tetrahydrofuran. The resulting mixture was stirred at room temperature for one hour and then heated at reflux for 20 hours. The mixture was cooled and sodium sulfate decahydrate was cautiously added portionwise to the mixture until it was colorless. The mixture was stirred for 30 minutes. The mixture was filtered and the filter was washed with ether. The filtrate was evaporated in vacuo to yield 29 g (99% yield) of a liquid. The liquid was distilled by Kugelrohr distillation, bp 85° C./0.070 mm of mercury, to give the desired product as a colorless liquid.

Workup

  1. additionwas added, at room temperature
  2. temperatureheated
  3. temperatureat reflux for 20 hours
  4. temperatureThe mixture was cooled
  5. stirringThe mixture was stirred for 30 minutes
  6. filtrationThe mixture was filtered
  7. washthe filter was washed with ether
  8. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-e5a5a0375d5d4886b27d6db3b8b8b55c
Source dataset
uspto-grants-1986_11
Patent number
US04623662

Reaction notes

Loading…