p-Fluoronitrobenzene → HCID 67442554, compound

HRID 882723Notes

Reaction equation

HRID 882723 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[NH:4][CH2:3][CH2:2]2.[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.C(OCCOCC)C>C(OCC)C>[FH:10].[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([N:4]2[CH:5]3[CH2:8][CH2:9][N:1]([CH2:7][CH2:6]3)[CH2:2][CH2:3]2)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 12375Ethylene glycol diethyl etherHCID 3984071,4-Diazabicyclo(3.2.2)nonane

Product 1

HCID 67442554HCID 67442554, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 1,4-diazabicyclo[3.2.2]nonane (20.2 g, 160 mmol), 1-fluoro-4-nitrobenzene (17.5 ml, 163.3 mmol) and ethylene glycol diethyl ether (160 ml) was stirred at 135° C. for 18 hours. The mixture was cooled to room-temperature and diethyl ether (100 ml) was added. The mixture was filtered and the product was isolated by filtration. Yield 24.8 g (58%). Mp. 122-129° C.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customthe product was isolated by filtration

Sources & evidence

ORD record
ord-6b7b217f631d45a9a377d9f508919d10
Source dataset
uspto-grants-2012_08
Patent number
US08236793B2

Reaction notes

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