Morpholine → HCID 19348259, compound

HRID 1637289Notes

Reaction equation

HRID 1637289 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]1[CH:22]2[CH2:23][C:24](=O)[CH2:25][C:20]3[C:21]2=[C:16]([CH:17]=[CH:18][CH:19]=3)[NH:15]1>C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+].[Ti](Cl)(Cl)(Cl)Cl>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]1[CH:22]2[CH2:23][CH:24]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH2:25][C:20]3[C:21]2=[C:16]([CH:17]=[CH:18][CH:19]=3)[NH:15]1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 19348365HCID 19348365, compound

Product 1

HCID 19348259HCID 19348259, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6212ChloroformSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Morpholine (0.51 ml) was dissolved in an anhydrous chloroform (5 ml) and to the solution was added dropwise a solution of titanium tetrachloride (98 μl) in anhydrous chloroform (2 ml) under cooling with ice, followed by addition of the compound (0.34 g) obtained in Example 252. The mixture was heated to reflux for 30 minutes and allowed to cool. The reaction mixture was diluted with saturated aqueous solution of sodium hydrogencarbonate and extracted twice with methylene chloride. The organic layers were combined, washed twice with water and once with saturated aqueous solution of sodium chloride successively and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to yield 0.42 g of the titled compound as a crude brown oil. The compound was used in the subsequent reaction without further purification.

Workup

  1. temperatureunder cooling with ice
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 30 minutes
  4. temperatureto cool
  5. extractionextracted twice with methylene chloride
  6. washwashed twice with water and once with saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b917b3d487014d61949601c2e34d4727
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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