2-((4-Nitrobenzyl)oxy)tetrahydro-2H-pyran → 4-(2-Tetrahydropyranyloxymethyl)aniline

HRID 1858283Notes

Reaction equation

HRID 1858283 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[O:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 109006552-((4-Nitrobenzyl)oxy)tetrahydro-2H-pyran

Product 1

HCID 184721974-(2-Tetrahydropyranyloxymethyl)anilineYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 8.5 g (35.9 mmol) of 2-(4-nitrobenzyloxy)-tetrahydropyran in 150 ml of methanol was hydrogenated at room temperature and atmospheric pressure in the presence of 800 mg of 10% palladium on carbon for 8 hours. The catalyst was removed by filtration and the filtrate evaporated to give a dark yellow oil. Purification by flash column chromatography on silica gel using 1:2 ethyl acetate/hexane as eluent gave 4.8 g (65%) of 4-(tetrahydropyran-2-yloxymethyl)aniline as a pale yellow oil. [Mass spectrum (ESI) [MH+MeCN]+ =249].

Workup

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated
  4. customto give a dark yellow oil
  5. customPurification by flash column chromatography on silica gel using 1:2 ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-59aef4f37ccd4d3b9cf647ce46e3589f
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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