Phosphorus oxychloride → HCID 86759003, compound

HRID 1368694Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=3)[CH2:19][C:18]2=O)[CH2:13][CH2:12]1.P(Cl)(Cl)([Cl:35])=O>>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=3)[CH:19]=[C:18]2[Cl:35])[CH2:13][CH2:12]1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 86759004HCID 86759004, compound

Product 1

HCID 86759003HCID 86759003, compoundYield 97.9%

Procedure

A suspension of ethyl [1-[1-(2-fluorophenetyl)piperidin-4-yl]-2-oxoindolin-6-yl]acetate (32.5 g, 76.559 mmol) in phosphoryl chloride (75.0 ml) was refluxed under heating for 2.5 hours (after 30 min., the suspension was dissolved). After removing the solvent, ethyl acetate (100 ml) and a 2N aqueous sodium hydroxide solution were added thereto, to separate the organic layer. It was washed with a 2N aqueous sodium hydroxide solution, water and brine, and then added with anhydrous magnesium sulfate and activated clay. After filtering, the solvent was removed, to give the title compound (yield: 33.2 g, 74.952 mmol, 97.9%).

Workup

temperaturewas refluxed
temperatureunder heating for 2.5 hours (after 30 min.
dissolutionthe suspension was dissolved)
customAfter removing the solvent, ethyl acetate (100 ml)
additiona 2N aqueous sodium hydroxide solution were added
customto separate the organic layer
washIt was washed with a 2N aqueous sodium hydroxide solution, water and brine
additionadded with anhydrous magnesium sulfate
filtrationAfter filtering
customthe solvent was removed

Sources & evidence

ORD record: ord-38313741a25843c2866fccdb05666be3
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573384B1

Reaction notes

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