Benzylamine → HCID 18942951, compound

HRID 355572Notes

Reaction equation

HRID 355572 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]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H][H]>C(O)C.CCOCC.[Pd]>[CH2:16]([NH:23][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)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 661394-PhenoxybenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 18942951HCID 18942951, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Phenoxybenzaldehyde (10.0 g, 0.05 mol), excess benzyl amine 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 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.

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-9e18fce550bf4cc1af14f7f90389a7a6
Source dataset
uspto-grants-1998_11
Patent number
US05831115

Reaction notes

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