Morpholine → HCID 19805183, compound

HRID 1681576Notes

Reaction equation

HRID 1681576 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][C:15](=[O:34])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([C:24]23[CH2:33][CH:28]4[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]4)[CH2:25]2)[CH2:31]3)[CH:17]=1)[C:5]([O:7]CC=C)=[O:6].N1CCOCC1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][C:15](=[O:34])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([C:24]23[CH2:31][CH:30]4[CH2:29][CH:28]([CH2:27][CH:26]([CH2:32]4)[CH2:25]2)[CH2:33]3)[CH:17]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 19805164HCID 19805164, compound

Product 1

HCID 19805183HCID 19805183, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.35 g (5 mmoles) of the ester prepared in step 15 (b) above are dissolved in 50 ml of THF. Under a stream of nitrogen, 78.3 mg of tetrakis(triphenylphosphine) palladium (O) are added and then 4.4 ml (50 mmoles) of morpholine are slowly introduced. The reaction mixture is then stirred at ambient temperature for 2 hours and evaporated to dryness. The residue is ground in ethyl ether and the solid is filtered. The solid is then introduced into 10 ml of water, acidified to pH 1, extracted with a 3/1 mixture of ethyl ether and THF. The organic phase is decanted, washed with water, dried over magnesium sulfate and evaporated. The residue is ground in 50 ml of ethyl ether, filtered and dried. 1.6 g (70% yield) 277° C. are obtained.

Workup

  1. customevaporated to dryness
  2. filtrationthe solid is filtered
  3. additionThe solid is then introduced into 10 ml of water
  4. extractionextracted with a 3/1 mixture of ethyl ether and THF
  5. customThe organic phase is decanted
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. filtrationfiltered
  10. customdried
  11. custom1.6 g (70% yield) 277° C. are obtained

Sources & evidence

ORD record
ord-26fa7e0f9769489da048250a40709887
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

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