p-Fluoronitrobenzene → HCID 68194563, compound

HRID 2370660Notes

Reaction equation

HRID 2370660 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH2:20]1[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:22][N:21]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CS(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:26]2[CH2:27][CH2:28][C:23]3([CH2:22][N:21]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH2:20]3)[CH2:24][CH2:25]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 23282935tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate

Product 1

HCID 68194563HCID 68194563, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-fluoro-4-nitrobenzene (0.155 ml, 1.458 mmol) in DMSO was added N,N-diisopropylethylamine (0.926 ml, 5.30 mmol) followed by tert-butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate (300 mg, 1.326 mmol). The reaction mixture was heated to 100° C. overnight, and cooled to room temperature. The reaction mixture was quenched with 75 mL water, filtered, washed with water and dried over high-vac to provide the title compound. MS (ESI+) m/z 348.1 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction mixture was quenched with 75 mL water
  3. filtrationfiltered
  4. washwashed with water
  5. customdried over high-vac

Sources & evidence

ORD record
ord-030a2d5bb6dc431f9bd400b7f8c5fe4d
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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