Isobutylamine → HCID 10587138, compound

HRID 1781139Notes

Reaction equation

HRID 1781139 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([NH2:20])[CH:17]([CH3:19])[CH3:18].[H][H]>C(O)C.CCOCC.[Pd]>[CH2:16]([NH:20][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1)[CH:17]([CH3:19])[CH3:18]

Participants

7

Reactant 3

HCID 6558IsobutylamineHCID 661394-PhenoxybenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 10587138HCID 10587138, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Phenoxybenzaldehyde (10.0 g, 0.05 mmol), excess isobutylamine and 1.0 g of 10% Pd/O in 200 mL of ethanol were stirred under an inert atmosphere for 16 hours followed by an atmosphere of hydrogen for 16 hours. After removal of the catalyst by filtration through Celite®, the filtrate was concentrated under reduced pressure to give the crude product as an oil. The oil was dissolved in ether and precipitated by treatment with anhydrous HCl. The solid was filtered, washed with ether, and partitioned between ethyl acetate and 1M NaOH. The ethyl acetate solution was washed with brine, dried over Na2SO4, and evaporated to give the title compound in 93% yield.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration through Celite®
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give the crude product as an oil
  5. customprecipitated by treatment with anhydrous HCl
  6. filtrationThe solid was filtered
  7. washwashed with ether
  8. custompartitioned between ethyl acetate and 1M NaOH
  9. washThe ethyl acetate solution was washed with brine
  10. dry with materialdried over Na2SO4
  11. customevaporated

Sources & evidence

ORD record
ord-794cb843b0f04a4eac209e5d6c1d7157
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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