Water → Piperidine, 1-methyl-4-(4-nitrophenoxy)-4-phenyl-

HRID 2285914Notes

Reaction equation

HRID 2285914 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+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.O>CS(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([O:8][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=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 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 786701-Methyl-4-phenylpiperidin-4-ol

Product 1

HCID 3060390Piperidine, 1-methyl-4-(4-nitrophenoxy)-4-phenyl-Yield 48.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1-methyl-4-phenyl-4-piperidinol (7.65 g, 40 mM) in dry DMSO (100 ml) was treated with sodium hydride (2.0 g of a 50% dispersion in oil, 42 mM). The reaction mixture was stirred for 1 hour then treated with 4-fluoronitrobenzene (5.65 g, 40 mM). After 24 hours the reaction mixture was poured on to water (500 ml) and extracted with ether (4×500 ml). The organic extracts were washed with brine, dried and the solvents removed under reduced pressure. Recrystallisation of the residue from IPA gave the title compound (6.1 g) m.p. 136°-8°.

Workup

  1. extractionextracted with ether (4×500 ml)
  2. washThe organic extracts were washed with brine
  3. customdried
  4. customthe solvents removed under reduced pressure
  5. customRecrystallisation of the residue from IPA

Sources & evidence

ORD record
ord-e3b6909eacc74f5098490af22d69aecc
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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