Isobutylamine → HCID 10587138, compound

HRID 1957325Notes

Reaction equation

HRID 1957325 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 mol), excess isobutylamine and 1.0 g of 10% Pd/C 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 a filter and (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
  3. filtrationa filter
  4. concentration(CELITE®), the filtrate was concentrated under reduced pressure
  5. customto give the crude product as an oil
  6. customprecipitated by treatment with anhydrous HCl
  7. filtrationThe solid was filtered
  8. washwashed with ether
  9. custompartitioned between ethyl acetate and 1M NaOH
  10. washThe ethyl acetate solution was washed with brine
  11. dry with materialdried over Na2SO4
  12. customevaporated

Sources & evidence

ORD record
ord-c8bb3752602f43d8bd1e1bcd4e1b0c95
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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