HCID 86691244, compound → HCID 86691243, compound

HRID 2038224Notes

Reaction equation

HRID 2038224 reaction equation
[CH2:1]([O:3][CH2:4][CH:5]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH2:6][N:7](CC1C=CC(OC)=CC=1)CC1C=CC(OC)=CC=1)[CH3:2]>[Pd].C(O)(C)(C)C>[CH2:1]([O:3][CH2:4][CH:5]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH2:6][NH2:7])[CH3:2]

Participants

4

Reactant 1

HCID 86691244HCID 86691244, compound

Product 1

HCID 86691243HCID 86691243, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

Combine 3-ethoxy-N,N-bis[(4-methoxyphenyl)methyl]-2-(2-pyridyloxy)propan-1-amine (1.05 g, 2.41 mmol), palladium/carbon (5%, 0.11 g, 0.05 mmol), and tert-butyl alcohol (15 mL). Purge with hydrogen gas 3 times and then stir the mixture at 50° C. under an atmosphere of hydrogen gas for 4 days. Filter the reaction through a Celite® plug and rinse the plug with EtOAc (2×30 mL). Collect the filtrate and concentrate under reduced pressure to afford the title compound (0.42 g, 89.0%) as a yellow oil. MS (m/z): 197 (M+1).

Workup

  1. customPurge with hydrogen gas 3 times
  2. filtrationFilter
  3. customthe reaction through a Celite® plug
  4. washrinse the plug with EtOAc (2×30 mL)
  5. customCollect the filtrate
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-439e851f78084c0ba142323c4f0e3b90
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

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