Ethyl Acetate → Decylamine

HRID 337558Notes

Reaction equation

HRID 337558 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH2:14][NH:15]C2CC2)C=[C:7](/[CH:9]=[CH:10]/[CH2:11]OC)[CH:8]=1.[CH3:19]COC(C)=O>[Pd]>[CH3:19][CH2:11][CH2:10][CH2:9][CH2:7][CH2:8][CH2:3][CH2:4][CH2:5][CH2:14][NH2:15]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 66899770HCID 66899770, compound

Product 1

HCID 8916Decylamine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of N-({3-(methyloxy)-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)cyclopropanamine (1 eq.) from the previous step in EtOAc (0.04 M) was added palladium (10% w/w over activated carbon, 0.1 eq). The vessel was evacuated and back filled with hydrogen. The reaction suspension was then stirred under a balloon atmosphere of hydrogen for 1.5 h. The reaction was quenched with dichloromethane and filtered through a bed of celite. The insolubles were washed further with EtOAc and methanol. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil.

Workup

  1. customThe vessel was evacuated
  2. additionback filled with hydrogen
  3. customThe reaction was quenched with dichloromethane
  4. filtrationfiltered through a bed of celite
  5. washThe insolubles were washed further with EtOAc and methanol

Sources & evidence

ORD record
ord-90ea42f1ce0b432d88a0faa27619dcf6
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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