(4-Methoxy-3-nitro-phenyl)-methyl-(tetrahydro-pyran-4-yl)-amine → HCID 22736961, compound

HRID 51897Notes

Reaction equation

HRID 51897 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:16])[CH:10]2[CH2:15][CH2:14]OCC2)=[CH:5][C:4]=1[N+:17]([O-])=O>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:16])[CH2:10][CH:15]2[CH2:14][CH2:1][O:2][CH2:3][CH2:4]2)=[CH:5][C:4]=1[NH2:17]

Participants

4

Reactant 1

HCID 22736985(4-Methoxy-3-nitro-phenyl)-methyl-(tetrahydro-pyran-4-yl)-amine

Product 1

HCID 22736961HCID 22736961, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 0.73 g (2.74 mmol) (4-methoxy-3-nitro-phenyl)-methyl-(tetrahydro-pyran-4-yl)-amine in 50 ml methanol was added 15 mg 10% palladium on charcoal and the mixture was then stirred for 18 hours at room temperature under an atmosphere of hydrogen. The mixture was then filtered and the filtrate concentrated in vacuo to afford 0.3520 g (54%) 4-methoxy-N1-methyl-N1-(tetrahydro-pyran-4-ylmethyl)-benzene-1,3-diamine as an off-white solid. Mp.: 97-99° C.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2d507111f11941d687f78fa1f7ed963a
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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