HCID 59442047, compound → HCID 59442050, compound

HRID 1014346Notes

Reaction equation

HRID 1014346 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([O:21][CH3:22])[CH:13]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:22][O:21][C:14]1[CH:13]=[C:12]([O:11][CH2:10][CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:17]=[CH:16][C:15]=1[NH2:18]

Participants

4

Reactant 1

HCID 59442047HCID 59442047, compound

Product 1

HCID 59442050HCID 59442050, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-methyl-4-(3-{[3-(methyloxy)-4-nitrophenyl]oxy}propyl)piperazine (1.8 g, 5.8 mmol) was dissolved in methanol (75 mL) and cycled through the H-Cube using a Pd/C cartridge. After 60 min of cycling through the system, the solvent was removed under reduced pressure. NMR indicates starting material still present so residue was dissolved in ethanol and 5% platinum on carbon (200 mg) was added and subjected to a H2 balloon for 16 h. At this time the reaction mixture was filtered through celite which was washed with methanol. The solvents were evaporated under reduced pressure to afford 2-(methyloxy)-4-{[3-(4-methyl-1-piperazinyl)propyl]oxy}aniline (1.1 g, 3.75 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.83 (d, J=5.68 Hz, 2 H) 2.41-2.51 (m, 3 H overlaying with DMSO peak) 2.51-2.99 (m, 10 H) 3.68 (s, 3 H) 3.83 (t, J=6.23 Hz, 2 H) 6.24 (dd, J=8.42, 2.56 Hz, 1 H) 6.39 (d, J=2.47 Hz 1 H) 6.49 (d, J=8.42 Hz, 1 H). ESIMS (M+H)+=311.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionwas dissolved in ethanol
  3. addition5% platinum on carbon (200 mg) was added
  4. waitsubjected to a H2 balloon for 16 h
  5. filtrationAt this time the reaction mixture was filtered through celite which
  6. washwas washed with methanol
  7. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-99dbd508f9924f219352f19021ef9850
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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