p-Fluoronitrobenzene → 8-(4-Nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1791910Notes

Reaction equation

HRID 1791910 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1>O>[CH2:3]1[O:4][C:5]2([CH2:10][CH2:9][N:8]([C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[CH2:7][CH2:6]2)[O:1][CH2:2]1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 81531Diisopropylethylamine

Product 1

HCID 71470798-(4-Nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 80.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,4-Dioxa-8-azaspiro[4,5]decane (7.88 g) was dissolved in N-methyl-2-pyrrolidine (50 mL), and diisopropylethylamine (9.5.8 mL) and 4-fluoronitrobenzene (7.06 g) were successively added. The mixture was stirred at room temperature for 2 hr. The reaction mixture was added to iced water, and the precipitated solid was collected by filtration to give N-(4-nitrophenyl)-4-piperidone ethylene ketal (10.6 g) as a yellow powder.

Workup

  1. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-83132976d59148e8bea04b988527ffdb
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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