Morpholine → HCID 21110134, compound

HRID 1766367Notes

Reaction equation

HRID 1766367 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[C:11]([CH3:26])=[C:10]2[C:27]([O:29]CC=C)=[O:28])=[CH:5][CH:4]=1)#[N:2].N1CCOCC1>O1CCCC1.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]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)[C:11]([CH3:26])=[C:10]2[C:27]([OH:29])=[O:28])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 21110148HCID 21110148, compound

Product 1

HCID 21110134HCID 21110134, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl 4-(4-cyanophenyl)-2-methyl-6-oxo-1-[3-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxylate (Example 46) (1.00 g, 2.27 mmol) and tetrakis(triphenylphosphin)-palladium(0) (68 mg, 0.059 mmol) in tetrahydrofuran (50 ml) is slowly added morpholine (3.36 g, 38.6 mmol). After stirring at room temperature for 1 h, the reaction mixture is quenched with water (50 ml). The basic solution (pH ca. 10) is neutralised with 1 N hydrochloric acid, and the aqueous phase is extracted with ethyl acetate (2×100 ml). The combined organic layers are washed with water, dried, and the solvent is removed in vacuo to yield pure product.

Workup

  1. customthe reaction mixture is quenched with water (50 ml)
  2. extractionthe aqueous phase is extracted with ethyl acetate (2×100 ml)
  3. washThe combined organic layers are washed with water
  4. customdried
  5. customthe solvent is removed in vacuo
  6. customto yield pure product

Sources & evidence

ORD record
ord-e34af13d39f84be9b5952bfd6d4ea492
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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