Water → 5-(Morpholin-4-yl)-2,3-dihydro-1H-inden-1-one

HRID 1362695Notes

Reaction equation

HRID 1362695 reaction equation
CN1CCCC1=O.F[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[CH2:13][CH2:12]2.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.O>C(OCC)(=O)C>[N:19]1([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12]3)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 13387N-methyl-2-pyrrolidoneHCID 1365375-Fluoro-1-indanone

Product 1

HCID 461728755-(Morpholin-4-yl)-2,3-dihydro-1H-inden-1-oneYield 77.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 1-methyl-2-pyrrolidone (10 mL) solution of 5-fluoroindanone (1.97 g) and morpholine (1.71 g) was agitated at 100° C. for 26 hours and 30 minutes. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system), and 2.20 g of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-b674a8325c0949b39c3aacc36979e191
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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