p-Fluoronitrobenzene → Tert-butyl 4-((4-nitrophenyloxy)methyl)piperidine-1-carboxylate

HRID 1079387Notes

Reaction equation

HRID 1079387 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 516892Sodium BicarbonateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 23366891Tert-butyl 4-((4-nitrophenyloxy)methyl)piperidine-1-carboxylateYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-tert-Butyloxycarbonyl-4-hydroxymethylpiperidine (2.8 g) was dissolved in dimethylformamide (10 ml), followed by stirring for 30 minutes. To the mixture was added p-fluoronitrobenzene (2.1 g), followed by stirring at room temperature overnight. Aqueous saturated solution of sodium bicarbonate was added to the mixture which was extracted with methylene chloride (50 ml×3). The combined organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (developing solvent: hexane/ethylacetate=5/1 (v/v)) to obtain 1-tert-butyloxycarbonyl-4-[(4-nitrophenyloxy)methyl]piperidine (1.9 g) as pale yellow crystals, m.p. 130°-131° C.

Workup

  1. stirringby stirring at room temperature overnight
  2. extractionwas extracted with methylene chloride (50 ml×3)
  3. washThe combined organic layer was washed with saturated saline
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by silica gel column chromatography (developing solvent: hexane/ethylacetate=5/1 (v/v))

Sources & evidence

ORD record
ord-367dea406add457db009002abaec1440
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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