Morpholine → 4-Morpholinocarbonyl-2-(1-naphthylmethylene)butyric acid

HRID 1768594Notes

Reaction equation

HRID 1768594 reaction equation
[C:1]1([CH:11]=[C:12]2[CH2:18][CH2:17][C:16](=[O:19])[O:15][C:13]2=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH: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:16](=[O:19])[CH2:17][CH2:18][C:12](=[CH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:13]([OH:15])=[O:14])[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 544510142-(1-Naphthylmethylene)glutaric anhydride

Product 1

HCID 538910904-Morpholinocarbonyl-2-(1-naphthylmethylene)butyric acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.5 g (30 mmole) of 2-(1-naphthylmethylene)glutaric anhydride (prepared as described above) were dissolved in 70 ml of methylene chloride, and 2.85 ml (33 mmole) of morpholine were added to the resulting solution. The mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was washed with a 5% v/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate and freed from the solvent by evaporation under reduced pressure, to give 10.0 g (30 mmole) of 5-morpholino-2-(1-naphthylmethylene)-5-oxopentanoic acid.

Workup

  1. washAt the end of this time, the reaction mixture was washed with a 5% v/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride, in that order
  2. dry with materialafter which it was dried over anhydrous sodium sulfate
  3. customfreed from the solvent by evaporation under reduced pressure

Sources & evidence

ORD record
ord-cbb04b06ee784a73be62dd7f7cd6b3dd
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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