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

HRID 1768599Notes

Reaction equation

HRID 1768599 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]1([CH:17]=[C:18]2[CH2:24][CH2:23][C:22](=[O:25])[O:21][C:19]2=[O:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[O:4]1[CH2:5][CH2:6][N:1]([C:22]([CH2:23][CH2:24][C:18](=[CH:17][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[C:19]([OH:21])=[O:20])=[O:25])[CH2:2][CH2:3]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

2.85 ml (33 mmole) of morpholine were added to a solution of 7.5 g (30 mmole) of the 2-(1-naphthylmethylene)glutaric anhydride prepared as described above dissolved in 70 ml of methylene chloride, and the mixture was stirred at room temperature for 4 hours. It was then washed 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 solvent was then removed by distillation under reduced pressure, to give 10.0 g (30 mmole) of 4-morpholinocarbonyl-2-(1-naphthylmethylene)butyric acid.

Workup

  1. customprepared
  2. washIt was then washed with a 5% w/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-2dfa7b70640b45589f7a52bb67c77565
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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