Water → 2-Allyloxymethyl-4-n-propylmorpholine

HRID 437186Notes

Reaction equation

HRID 437186 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]1[O:11][CH2:10][C:9](=O)[N:8]([CH2:13][CH2:14][CH3:15])[CH2:7]1)[CH:2]=[CH2:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH2:1]([O:4][CH2:5][CH:6]1[O:11][CH2:10][CH2:9][N:8]([CH2:13][CH2:14][CH3:15])[CH2:7]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 538376442-Allyloxymethyl-4-n-propylmorpholin-5-one

Product 1

HCID 214304122-Allyloxymethyl-4-n-propylmorpholine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-allyloxymethyl-4-n-propylmorpholin-5-one (65 g.) in dry ether (100 ml.) is added slowly with stirring to a suspension of lithium aluminium hydride (17.5 g.) in dry ether (700 ml.). The rate of addition is adjusted so that the reaction mixture refluxes gently. When the addition is complete the reaction mixture is stirred at ambient temperature (18°-20° C.) for 18 hours and then water (90 ml.) is added very carefully dropwise to decompose the complex and excess of lithium aluminium hydride. The ethereal solution is filtered and the solid residue is washed with ether. The filtrate and ethereal washings are combined, dried (Na2SO4), filtered and the ether evaporated. The product, 2-allyloxymethyl-4-n-propylmorpholine is obtained as an oil b.p. 80°-90° C. at 1 m.m. which forms a hydrogen oxalate, m.p. 125°-127° C.

Workup

  1. additionThe rate of addition
  2. additionWhen the addition
  3. filtrationThe ethereal solution is filtered
  4. washthe solid residue is washed with ether
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe ether evaporated

Sources & evidence

ORD record
ord-1e7be51f309a46c587a61cccdf5a2c56
Source dataset
uspto-grants-1977_06
Patent number
US04029786

Reaction notes

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