Methanol → Dioleylamine

HRID 1957462Notes

Reaction equation

HRID 1957462 reaction equation
C([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([NH-:38])=O)CCCCCCC/C=C\CCCCCCCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.O>C1COCC1.C(Cl)Cl>[CH2:19]([NH:38][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]/[CH:28]=[CH:27]\[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178442858HCID 178442858, compound

Product 1

HCID 11214516Dioleylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-oleyloleoylamide (prepared above) in THF (100 mL) was warmed to 40° C. Lithium aluminum hydride was slowly added until violent evolution of gas ceased. The reaction mixture was heated to reflux for one hour and then cooled to room temperature. Methanol (100 mL) was slowly added, followed by water (200 mL). Methylene chloride was added and the resultant suspension was stirred for fifteen minutes. The slurry was filtered and the precipitate was washed with ethanolmethylene chloride (50:50, 50 mL, 2×). The combined filtrates were extracted with methylene chloride. The organic fraction was dried over magnesium sulphate, filtered and the solvent was removed under vacuum. The residue was passed down a silica gel column (150 g) using 5% methanol in methylene chloride as the eluent, to provide dioleylamine as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for one hour
  3. filtrationThe slurry was filtered
  4. washthe precipitate was washed with ethanolmethylene chloride (50:50, 50 mL, 2×)
  5. extractionThe combined filtrates were extracted with methylene chloride
  6. dry with materialThe organic fraction was dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-f172915884e6408d902fc2c9b9ff1e54
Source dataset
uspto-grants-1998_07
Patent number
US05785992

Reaction notes

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