HCID 22736995, compound → HCID 22736961, compound

HRID 51889Notes

Reaction equation

HRID 51889 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:17])[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][C:4]=1[N+:18]([O-])=O>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:17])[CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)=[CH:5][C:4]=1[NH2:18]

Participants

4

Reactant 1

HCID 22736995HCID 22736995, compound

Product 1

HCID 22736961HCID 22736961, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3.5 g (12.5 mmol) (4-methoxy-3-nitro-phenyl)-methyl-(tetrahydro-pyran-4-ylmethyl)-amine in 230 ml methanol was added 70 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 2.20 g (70%) 4-methoxy-N1-methyl-N1-(tetrahydropyran-4-ylmethyl)-benzene-1,3-diamine as a dark brown oil. ES-MS m/e (%): 251 (M+H+, 100).

Workup

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

Sources & evidence

ORD record
ord-f38179065dd642c597e1d36ca259032e
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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