p-Fluoronitrobenzene → HCID 20536592, compound

HRID 2285909Notes

Reaction equation

HRID 2285909 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1>CS(C)=O>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([O:20][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 973334-Piperidinol, 1-benzyl-4-phenyl-

Product 1

HCID 20536592HCID 20536592, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1-benzyl-4-hydroxy-4-phenylpiperidine (5.35 g, 20 mM) in dry DMSO (50 ml) was treated with a 50% sodium hydride dispersion (960 mg, 20 mM) followed by 4-fluoronitrobenzene (2.82 g, 20 mM). After 24 hours the reaction mixture was partitioned between water (200 ml) and ether (200 ml). The aqueous layer was extracted with ether (2×200 ml) and the combined organic layers washed with water (200 ml). The organic phase was dried and the solvent removed under reduced pressure. Recrystallisation of the residue from IPA gave the title compound (3.5 g) m.p. 135°-7° C.

Workup

  1. customAfter 24 hours the reaction mixture was partitioned between water (200 ml) and ether (200 ml)
  2. extractionThe aqueous layer was extracted with ether (2×200 ml)
  3. washthe combined organic layers washed with water (200 ml)
  4. customThe organic phase was dried
  5. customthe solvent removed under reduced pressure
  6. customRecrystallisation of the residue from IPA

Sources & evidence

ORD record
ord-b0db8264c5ee4b20806882ec09f3250d
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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