Water → HCID 20289414, compound

HRID 1413997Notes

Reaction equation

HRID 1413997 reaction equation
[CH2:1]([N:5]1[CH2:10][CH:9]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:8][CH:7]([CH2:20][OH:21])[CH2:6]1)[CH2:2][CH2:3][CH3:4].Cl[CH2:23][C:24]([N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])=[O:25].[OH-].[Na+].O>CS(C)=O>[CH2:1]([N:5]1[CH2:10][CH:9]([CH2:11][O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:8][CH:7]([CH2:20][O:21][CH2:23][C:24]([N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])=[O:25])[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2196472-chloro-N,N-dipropylacetamideHCID 20289409HCID 20289409, compound

Product 1

HCID 20289414HCID 20289414, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 16.2 g of 4-butyl-6-[(phenylmethoxy)methyl]-2-morpholinemethanol (0.055 mole) and 9.81 g of 2-chloro-N,N-dipropylacetamide (0.055 mole) are dissolved in 200 ml of dry dimethyl sulfoxide and the mixture stirred at room temperature under nitrogen. Slowly, 1.0 g of sodium hydroxide (0.04 mole) is added to the dimethyl sulfoxide mixture and the reaction allowed to stir at ambient temperature (23°). After stirring for 10 minutes an exothermic reaction begins to take place and an ice-bath is used to maintain the reaction temperature below 30°. After stirring for 1 hour the ice-bath is removed and the reaction allowed to stir at room temperature for 18 hours. The excess NaH is destroyed by adding 5 ml of methanol and the entire reaction mixture is then poured into 400 ml of water. The product is extracted with 3×125 ml portions of chloroform. The CHCl3 extracts are combined and washed with 4×300 ml portions of water. The CHCl3 layer is separated, dried over anhydrous Na2SO4, and the CHCl3 removed in vacuo yielding 22.4 g (94%) of the title compound as a yellow oil. The resulting oil is purified on a neutral Alumina III column (500 g), 40% chloroform/hexane yielding 12.9 g (54%) of product as a pale yellow oil. The 12.9 g of product are dried in vacuo (80° @0.2 mm) to give the desired product.

Workup

  1. stirringto stir at ambient temperature (23°)
  2. stirringAfter stirring for 10 minutes
  3. customan exothermic reaction
  4. temperatureto maintain the reaction temperature below 30°
  5. customis removed
  6. stirringto stir at room temperature for 18 hours
  7. customThe excess NaH is destroyed
  8. additionby adding 5 ml of methanol
  9. customthe entire reaction mixture
  10. extractionThe product is extracted with 3×125 ml portions of chloroform
  11. washwashed with 4×300 ml portions of water
  12. customThe CHCl3 layer is separated
  13. dry with materialdried over anhydrous Na2SO4
  14. customthe CHCl3 removed in vacuo

Sources & evidence

ORD record
ord-bda85b62eaea457d98dc943621a16fa6
Source dataset
uspto-grants-1981_02
Patent number
US04252801

Reaction notes

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