1,4-Cyclohexadiene → 2-(4-Oxazol-4-yl-phenoxy)-ethylamine

HRID 2120276Notes

Reaction equation

HRID 2120276 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[N:21]=[CH:22][O:23][CH:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.C1CC=CCC=1>CO.[Pd]>[O:23]1[CH: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)[N:21]=[CH:22]1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 20620891[2-(4-Oxazol-4-yl-phenoxy)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 112064972-(4-Oxazol-4-yl-phenoxy)-ethylamineYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of 234.0 g (0.692 mol) of [2-(4-oxazol-4-yl-phenoxy)-ethyl]-carbamic acid benzyl ester, 295.1 ml (3.097 mol) of 1,4-cyclohexadiene, and 93.60 g of 10% Pd/C (50% water wet) in 5.6 l of methanol was stirred at room temperature for about twenty-two hours. The mixture was filtered through a pad of diatomaceous earth (13×3 cm), and the filter cake was then washed with 12 l of 100:1 v/v methanol/triethylamine. The filtrate was evaporated in vacuo, and to the residual solid was added 250 ml of toluene. The mixture was stirred at room temperature for about thirty minutes, 2.5 l of hexanes was then added over a period of about five to ten minutes, and the resulting slurry was then stirred for about one hour. The mixture was filtered, and the filter cake was then washed with a mixture of 1:10 toluene/hexanes (3×100 ml), and the solid was dried under vacuum at about 50° C. for about eighteen hours. The title compound (115 g, 81.5% yield) was obtained as a white powder.

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth (13×3 cm)
  2. washthe filter cake was then washed with 12 l of 100:1 v/v methanol/triethylamine
  3. customThe filtrate was evaporated in vacuo
  4. additionto the residual solid was added 250 ml of toluene
  5. stirringThe mixture was stirred at room temperature for about thirty minutes
  6. addition2.5 l of hexanes was then added over a period of about five to ten minutes
  7. stirringthe resulting slurry was then stirred for about one hour
  8. filtrationThe mixture was filtered
  9. washthe filter cake was then washed with a mixture of 1:10 toluene/hexanes (3×100 ml)
  10. customthe solid was dried under vacuum at about 50° C. for about eighteen hours

Sources & evidence

ORD record
ord-5a55fb4c6d0641748ea3f21de8e79511
Source dataset
uspto-grants-2004_02
Patent number
US06689888B2

Reaction notes

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