Water → 1-Decanamine, N-ethyl-

HRID 426503Notes

Reaction equation

HRID 426503 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:17][C:18](=O)[CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O>CCOCC>[CH2:7]([NH:17][CH2:18][CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 98880Acetamide, N-decyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 111830541-Decanamine, N-ethyl-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

15.4 g of lithium aluminium hydride were suspended in 300 ml of abs. ether under reflux. 61 g of N-decylacetamide (product of a) were dissolved in 300 ml of ether and the solution was added dropwise in the course of 2 hours to the solution heated to reflux. The heterogeneous mixture was stirred under reflux for 15 hours. Then 32 ml of water were added dropwise at room temperature in the course of 1 hour. After stirring for 30 minutes, the solid was collected by suction filtration and washed repeatedly with ether. The filtrate was evaporated and the residue distilled in a high vacuum. Yield: 35 g of a fraction with a boiling point of 62°-64° C. (0.2 torr).

Workup

  1. additionthe solution was added dropwise in the course of 2 hours to the solution
  2. temperatureheated to reflux
  3. temperatureunder reflux for 15 hours
  4. stirringAfter stirring for 30 minutes
  5. filtrationthe solid was collected by suction filtration
  6. washwashed repeatedly with ether
  7. customThe filtrate was evaporated
  8. distillationthe residue distilled in a high vacuum

Sources & evidence

ORD record
ord-4e1dac21007a434fb886c72bde6fed44
Source dataset
uspto-grants-1979_10
Patent number
US04169896

Reaction notes

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