1,4-Cyclohexadiene → 2-[4-(4-Methyl-oxazol-2-yl)-phenoxy]-ethylamine

HRID 49373

Reaction equation

HRID 49373 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:21][CH:22]=[C:23]([CH3:25])[N:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.C1CC=CCC=1>CO.[Pd]>[CH3:25][C:23]1[N:24]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][NH2:10])=[CH:15][CH:16]=2)[O:21][CH:22]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 12986049{2-[4-(4-Methyl-oxazol-2-yl)-phenoxy]-ethyl}-carbamic acid benzyl ester2×

Product 1

HCID 120719972-[4-(4-Methyl-oxazol-2-yl)-phenoxy]-ethylamineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound of Example 1, {2-[4-(4-Methyl-oxazol-2-yl)-phenoxy]-ethyl}-carbamic acid benzyl ester, (166 mg, 0.47 mmol) was dissolved in methanol (5 ml) and 10% Pd/C (50 mg) and 1,4-cyclohexadiene (192 mg, 2.4 mmol) were added to the resulting solution. The mixture was allowed to stir for about sixteen hours, and then it was filtered through diatomaceous earth, and the filter pad was washed with methanol. The filtrate was concentrated in vacuo to dryness, and the resulting material (92 mg, 90% yield), which was determined to be pure by 1H NMR, was used directly without further purification. LRMS ([M+H]+)=219.2.

Workup

  1. filtrationit was filtered through diatomaceous earth
  2. washthe filter pad was washed with methanol
  3. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-b8a149b034b44dceb24886fdb7e850f7
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Linked notes

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