Water → 1-[(Dimethylphosphinyl)methyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

HRID 1031544Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:9]=1[O:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH3:25][P:26]([CH2:29]Cl)([CH3:28])=[O:27].O>CN(C)C=O>[CH3:25][P:26]([CH2:29][N:14]1[CH2:15][CH2:16][CH:11]([O:10][C:9]2[C:17]([F:24])=[C:18]([F:23])[C:19]([F:22])=[C:20]([F:21])[C:8]=2[F:7])[CH2:12][CH2:13]1)([CH3:28])=[O:27]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring mixture of 9.0 g of potassium carbonate in 100 ml of dimethylformamide was added 8.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine and 9.5 g of dimethylphosphinylmethyl chloride. After stirring at 80° C. for 30 hours, the reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, evaporation afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane). The desired fractions were evaporated to yield a solid which was sublimed to afford 2.37 g (22.1%) of 1-[(dimethylphosphinyl)methyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine, m.p. 120°-123° C.

Workup

temperaturethe reaction mixture was cooled
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtering
customevaporation
customafforded a residue which
customwas purified by means of high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane)
customThe desired fractions were evaporated
customto yield a solid which

Sources & evidence

ORD record: ord-64533776b19e47e8a6a946d00e3fbf93
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04954511

Reaction notes

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