Morpholine → HCID 20220947, compound

HRID 1263238Notes

Reaction equation

HRID 1263238 reaction equation
[CH3:1][CH:2]([CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH2:3][C:4]([OH:6])=O.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>O1CCCC1>[CH3:1][CH:2]([CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH2:3][C:4]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[O:6]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10105638HCID 10105638, compound

Product 1

HCID 20220947HCID 20220947, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In anhydrous tetrahydrofuran was dissolved 6.9 g of the compound obtained in step (c) above, and 3 g of triethylamine and then 3.3 g of ethyl chlorocarbonate were added to the solution at 0° C. The mixture was stirred for 20 minutes. Into the liquid reaction mixture was dropped 3.1 g of morpholine at 0° C., and the mixture was stirred for 30 minutes. The liquid reaction mixture was extracted with n-hexane, and the extract was washed with water and dried. The solvent was removed by distillation and the residue was purified by column chromatography using silica gel to obtain 5.6 g of the intended compound in the form of an oil.

Workup

  1. customInto the liquid reaction mixture
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe liquid reaction mixture
  4. extractionwas extracted with n-hexane
  5. washthe extract was washed with water
  6. customdried
  7. customThe solvent was removed by distillation
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-dc836a9b53c9440e99ca7f156e80ad4f
Source dataset
uspto-grants-1984_06
Patent number
US04456603

Reaction notes

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