p-Fluoronitrobenzene → Piperidine, 1-methyl-4-(4-nitrophenoxy)-4-phenyl-

HRID 1156026Notes

Reaction equation

HRID 1156026 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].[H][H].F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1>CN(C)C=O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([O:8][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 786701-Methyl-4-phenylpiperidin-4-olHCID 178418361HCID 178418361, compound

Product 1

HCID 3060390Piperidine, 1-methyl-4-(4-nitrophenoxy)-4-phenyl-Yield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 54 g of 1-methyl-4-phenylpiperidin-4-ol in 200 ml of absolute dimethylformamide is added dropwise to a suspension of 12.6 g of sodium hydride (80% strength in oil) in 200 ml of absolute dimethylformamide at a temperature of 45° C., while stirring and with exclusion of moisture. During this addition, evolution of hydrogen occurs. When the addition has ended, the mixture is stirred at 50° C. for a further 2 hours and allowed to cool to room temperature. A solution of 49.4 g of 4-fluoronitrobenzene in 100 ml of absolute dimethylformamide is then added dropwise thereto. Stirring is continued for a further 2 hours, and the reaction mixture is then poured onto 800 ml of ice-water. The precipitate which forms is filtered off and washed with water. Recrystallization from 250 ml of ethanol yields 52 g of the title compound of m.p. 135° to 137° C.

Workup

  1. additionWhen the addition
  2. stirringthe mixture is stirred at 50° C. for a further 2 hours
  3. stirringStirring
  4. filtrationThe precipitate which forms is filtered off
  5. washwashed with water
  6. customRecrystallization from 250 ml of ethanol

Sources & evidence

ORD record
ord-b77a6acac1c9489fa83b1643f0311fbf
Source dataset
uspto-grants-1982_06
Patent number
US04333942

Reaction notes

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