Morpholine → HCID 54423361, compound

HRID 1736015Notes

Reaction equation

HRID 1736015 reaction equation
[H-].[Na+].[OH:3][CH:4]1[C:9]2[CH:10]=[C:11]([S:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])=[O:14])[S:12][C:8]=2[S:7](=[O:22])(=[O:21])[NH:6][CH2:5]1.Br[CH2:24][CH:25]=[CH:26][CH2:27]Br.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>CN(C=O)C>[OH:3][CH:4]1[C:9]2[CH:10]=[C:11]([S:13]([NH:16][C:17]([CH3:18])([CH3:19])[CH3:20])(=[O:14])=[O:15])[S:12][C:8]=2[S:7](=[O:22])(=[O:21])[N:6]([CH2:24][CH:25]=[CH:26][CH2:27][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH2:5]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 131802-Butene, 1,4-dibromo-HCID 24758Sodium hydrideHCID 22901902HCID 22901902, compound

Product 1

HCID 54423361HCID 54423361, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.113 g, 2.82 mmol) was added to a solution of the product from Example 1, Step F (0.80 g, 2.35 mmol) in anhydrous DMF (50 mL) under nitrogen. After 20 min, the reaction mixture was cooled (ice bath), 1,4-dibromo-2-butene (0.754 g, 3.53 mmol) was added and the mixture stirred for 2 h. Morpholine (5 mL) was added and the reaction mixture was stirred at ambient temperature for 18 h. DMF was evaporated under reduced pressure and the residue was mixed with a saturated solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4), filtered and evaporated to dryness. Chromatography on silica (ethyl acetate) gave the desired product as a viscous oil (0.65 g, 58%).

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at ambient temperature for 18 h
  3. customDMF was evaporated under reduced pressure
  4. additionthe residue was mixed with a saturated solution of sodium bicarbonate (100 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-5c886e29dc5249a8a7433886065c21a2
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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