Aluminium lithium hydride → 2,3-Dioleyloxypropylamine

HRID 376413Notes

Reaction equation

HRID 376413 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:25][CH:26]([CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:27][N:28]=[N+]=[N-])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O1CCCC1>[CH2:7]([O:25][CH:26]([CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:27][NH2:28])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 867518532,3-Dioleyloxypropyl azide

Product 1

HCID 110392282,3-DioleyloxypropylamineYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran was suspended 75 mg (2 mmol) of lithium aluminum hydride. While this suspension was held under ice-cooling, 1.03 g (1.7 mmol) of 2,3-dioleyloxypropyl azide was added dropwise and the mixture was stirred for 30 minutes. Then, the mixture was further stirred at ambient temperature for 2 hours. At completion of the reaction, the reaction mixture was poured in ice-water and extracted with ether and the extract was washed with water, dried, and concentrated. The residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 0.98 g (98%) of the title compound as colorless oil.

Workup

  1. temperaturecooling
  2. stirringThen, the mixture was further stirred at ambient temperature for 2 hours
  3. customAt completion of the reaction
  4. extractionextracted with ether
  5. washthe extract was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae5a30563ae84aae92180ad884459803
Source dataset
uspto-grants-2000_02
Patent number
US06020317

Reaction notes

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