p-Fluoronitrobenzene → HCID 69029219, compound

HRID 2382163Notes

Reaction equation

HRID 2382163 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 10340Sodium CarbonateHCID 2760465Ethyl 2-(piperidin-4-yl)acetate

Product 1

HCID 69029219HCID 69029219, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-(ethoxycarbonylmethyl)piperidine (0.011 mol) and 1-fluoro-4-nitrobenzene (0.011 mol) in DMSO (20 ml) was stirred in the presence of Na2CO3 (0.044 mol) during 2 hours at a temperature of 60° C. The reaction mixture was cooled to room temperature and poured into an ice/water mixture. The resulting precipitate was filtered and washed with water. The reaction product was purified by recrystallisation from a mixture of ethyl acetate and hexane, yielding [1-(4-nitro-phenyl)-piperidin-4-yl]-acetic acid ethyl ester (intermediate 3, mp. 83-85° C.).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customThe reaction product was purified by recrystallisation from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-86dfe0d763c747a1a2d90f1f0c22d565
Source dataset
uspto-grants-2012_09
Patent number
US08258304B2

Reaction notes

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