p-Fluoronitrobenzene → HCID 66670026, compound

HRID 1038738Notes

Reaction equation

HRID 1038738 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH:11][CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:18][N:15]1[CH2:16][CH2:17][CH:12]([O:11][C:7]2[CH:2]=[CH:3][CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 14797Potassium HydroxideHCID 660484-Piperidinol, 1-methyl-

Product 1

HCID 66670026HCID 66670026, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-fluoro-nitrobenzene (10 g, 71.0 mmol), 4-hydroxy-1-methyl-piperidine (16.6 ml, 141.8 mmol, 2 eq.), tetrabutylammonium bromide (4.6 g, 14.2 mmol, 0.2 eq.), toluene (50 ml) and a 25% aqueous solution of potassium hydroxide (50 ml) is stirred for 15 h at 60° C. The reaction mixture is cooled to RT and poured onto ice/water. The resulting suspension is filtered and the filtrate is extracted with EE. The organic phase is washed with 0.5 N HCl, brine, then dried (sodium sulfate), filtered, and concentrated to afford 6 g of the title compound. The aqueous layer is made neutral by addition of sodium bicarbonate and extracted with EE. The organic phase is washed with brine, dried (sodium sulfate), filtered, and concentrated to afford additional 10 g of the title compound: ESI-MS: 237.0 [MH]+; tR=2.61 min (purity: 90%, gradient J).

Workup

  1. additionpoured onto ice/water
  2. filtrationThe resulting suspension is filtered
  3. extractionthe filtrate is extracted with EE
  4. washThe organic phase is washed with 0.5 N HCl, brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-14d867f1aee148978134522474292ddb
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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