Morpholine → HCID 70048701, compound

HRID 1768578Notes

Reaction equation

HRID 1768578 reaction equation
[C:1]1(=[C:11]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[O:14][C:12]2=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C(Cl)Cl>[O:23]1[CH2:24][CH2:25][N:20]([C:15]([CH2:16][CH2:17][CH2:18][C:11](=[C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH2:2]2)[C:12]([OH:14])=[O:13])=[O:19])[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86748354HCID 86748354, compound

Product 1

HCID 70048701HCID 70048701, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.4 g (16.5 mmole) of 2-(1-naphthylidene)adipic anhydride (prepared as described above) dissolved in 80 ml of methylene chloride were added 1.58 ml (18.2 mmole) of morpholine, and the mixture was stirred at room temperature for 14 hours. At the end of this time, the reaction mixture was washed, in turn, with a 5% w/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The mixture was then freed from the solvent by evaporation under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: a 30: 1 by volume mixture of methylene chloride and methanol), to afford 1.12 g of 5-morpholinocarbonyl-2-(1-naphthylidene)pentanoic acid.

Workup

  1. washAt the end of this time, the reaction mixture was washed, in turn, with a 5% w/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe mixture was then freed from the solvent by evaporation under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent
  5. additiona 30: 1 by volume mixture of methylene chloride and methanol),

Sources & evidence

ORD record
ord-2c96cbe6ad1a400eb06887b6a2678c88
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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