Water → 1-Methyl-4-(2-nitrophenoxy)-4-phenylpiperidine

HRID 2285907Notes

Reaction equation

HRID 2285907 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][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].O>CS(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([O:8][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])([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 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 786701-Methyl-4-phenylpiperidin-4-ol

Product 1

HCID 205426131-Methyl-4-(2-nitrophenoxy)-4-phenylpiperidineYield 32.8%

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 50% dispersion in oil 42 mM), the mixture stirred for 1 hour and then treated with 2-fluoronitrobenzene (5.65 g, 40 mM). After 24 hours the reaction mixture was poured in to water (500 ml) and extracted with ether (2×500 ml). The organic extract was washed with brine, dried and the solvents removed under reduced pressure. Recrystallisation of the residue from cyclohexane gave the title compound (4.1 g) m.p. 80°-2° C.

Workup

  1. extractionextracted with ether (2×500 ml)
  2. extractionThe organic extract
  3. washwas washed with brine
  4. customdried
  5. customthe solvents removed under reduced pressure
  6. customRecrystallisation of the residue from cyclohexane

Sources & evidence

ORD record
ord-0238560c4095449e8427ff84ff963ae2
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

Loading…