Morpholine → HCID 54294057, compound

HRID 726464Notes

Reaction equation

HRID 726464 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:20]1[CH:29]=[CH:28][C:27]2[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=2[CH:21]=1)[C:5]([NH:7][C:8]1[CH:19]=[CH:18][C:11]([C:12]([O:14]CC=C)=[O:13])=[CH:10][CH:9]=1)=[O:6].N1CCOCC1>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][O:2][N:3]=[C:4]([C:20]1[CH:29]=[CH:28][C:27]2[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=2[CH:21]=1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:18][CH:19]=1)=[O:6]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 54404307HCID 54404307, compound

Product 1

HCID 54294057HCID 54294057, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

1.4 g (3.1 mmol) of the ester prepared in (a), 190 mg (0.16 mmol) of tetrakis(triphenylphosphine)-palladium(O) and 50 ml of TEF were introduced into a three-necked flask under a nitrogen stream. 2.7 ml (31 mmol) of morpholine were then added dropwise and the mixture was stirred at room temperature for 2 hours. The reaction medium was evaporated to dryness, taken up in water, acidified to pH 1, and extracted with ethyl ether, the organic phase was decanted off, washed with water, dried over magnesium sulfate and evaporated. The residue obtained was triturated in 50 ml of dichloromethane, filtered and dried. 1.2 g (95%) of 4-[α-methoxyimino-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetamido]benzoic acid of melting point 208°-209° C. were recovered.

Workup

  1. additionwere introduced into a three-necked flask under a nitrogen stream
  2. customThe reaction medium was evaporated to dryness
  3. extractionextracted with ethyl ether
  4. customthe organic phase was decanted off
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue obtained
  9. customwas triturated in 50 ml of dichloromethane
  10. filtrationfiltered
  11. customdried
  12. custom1.2 g (95%) of 4-[α-methoxyimino-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetamido]benzoic acid of melting point 208°-209° C. were recovered

Sources & evidence

ORD record
ord-51fb64cdc99549068d40576500b0d11c
Source dataset
uspto-grants-1998_01
Patent number
US05709867

Reaction notes

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