2-(4-Methyl-3-nitrobenzyloxy)tetrahydropyran → 2-Methyl-5-(tetrahydropyran-2-yloxymethyl)phenylamine

HRID 1176417Notes

Reaction equation

HRID 1176417 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[CH:4][C:3]=1[N+:16]([O-])=O>C(O)C.[Pd]>[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[CH:4][C:3]=1[NH2:16]

Participants

4

Reactant 1

HCID 685034882-(4-Methyl-3-nitrobenzyloxy)tetrahydropyran

Product 1

HCID 685034442-Methyl-5-(tetrahydropyran-2-yloxymethyl)phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The solution of 12.3 g of 2-(4-methyl-3-nitrobenzyloxy)tetrahydropyran in 150 ml of ethanol is hydrogenated in the presence of 1.25 g of 10% Pd/C over 24 hours. The reaction mixture is filtered and the filtrate is concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.19 (1:2 EtOAc-heptane); Rt=2.72.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-0ebde2d9657f4b20ad2799b80a265210
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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