p-Fluoronitrobenzene → HCID 14649986, compound

HRID 1721852Notes

Reaction equation

[H-].[Na+].[C:3]([N:6]1[CH2:11][CH2:10][C:9]([OH:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4].F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1>CN(C)C=O>[C:3]([N:6]1[CH2:11][CH2:10][C:9]([O:18][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred suspension of sodium hydride (60% in oil, 1.00 g) in 50 ml of dimethylformamide was treated with a solution of 4.0 g of 1-acetyl-4-hydroxy-4-phenylpiperidine in 100 ml of dimethylformamide. The mixture was heated at 70° C. until evolution of gas had ceased. After cooled to ice bath temperature, a solution of 2.96 g of 1-fluoro-4-nitrobenzene in 40 ml of dimethylformamide was added, dropwise, and the reaction allowed to proceed for 20 hours. The reaction mixture was then poured into ice water and the aqueous suspension extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated to an oil. High pressure liquid chromatography of the oil (silica gel; elution with 20% ethyl acetate/dichloromethane) afforded 4.73 g (77.29%) of 1-acetyl-4-(4-nitrophenoxy)-4-phenylpiperidine, m.p. 145°-150° C.

Workup

temperatureAfter cooled to ice bath temperature
extractionthe aqueous suspension extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated to an oil
washHigh pressure liquid chromatography of the oil (silica gel; elution with 20% ethyl acetate/dichloromethane)

Sources & evidence

ORD record: ord-f3f423d25f6e4f0190d14f463c0ab7a5
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04853384

Reaction notes

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