Benzyl [1-(5-amino-[1,3,4]oxadiazol-2-yl)-3-phenylpropyl]carbamate → 5-(1-Amino-3-phenylpropyl)-[1,3,4]oxadiazol-2-ylamine

HRID 278033Notes

Reaction equation

HRID 278033 reaction equation
[NH2:1][C:2]1[O:6][C:5]([CH:7]([NH:16]C(=O)OCC2C=CC=CC=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][N:3]=1>CO.[Pd]>[NH2:16][CH:7]([C:5]1[O:6][C:2]([NH2:1])=[N:3][N:4]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 86757873Benzyl [1-(5-amino-[1,3,4]oxadiazol-2-yl)-3-phenylpropyl]carbamate

Product 1

HCID 226269395-(1-Amino-3-phenylpropyl)-[1,3,4]oxadiazol-2-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.33 g of benzyl [1-(5-amino-[1,3,4]oxadiazol-2-yl)-3-phenylpropyl]carbamate were dissolved in 50 ml of dry methanol at RT, treated under argon with hydrogenation catalyst (10% palladium on carbon), and hydrogenated at RT for 3 h. The reaction mixture was filtered off through Celite, the filtrate was concentrated under reduced pressure, and the residue was dried under high vacuum. 5-(1-Amino-3-phenylpropyl)-[1,3,4]oxadiazol-2-ylamine was obtained, which was employed in the next stage without further purification.

Workup

  1. filtrationThe reaction mixture was filtered off through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-52cfe1ab7fc84582bd6ab3fc8666b872
Source dataset
uspto-grants-2002_03
Patent number
US06358978B1

Reaction notes

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