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

HRID 49393

Reaction equation

HRID 49393 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]=[C:22]([CH3:25])[O:23][CH:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.C1CC=CCC=1>>[CH3:25][C:22]1[O:23][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]=1

Participants

3

Reactant 2

HCID 123431,4-CyclohexadieneHCID 20587951Benzyl-{2-[4-(2-methyl-oxazol-4-yl)-phenoxy]-ethyl]-carbamate

Product 1

HCID 98132202-[4-(2-Methyl-oxazol-4-yl)-phenoxy]-ethylamineYield 100.9%

Procedure

A round-bottomed flask containing benzyl-{2-[4-(2-methyl-oxazol-4-yl)-phenoxy]-ethyl}-carbamate (788 mg, 2.07 mmol) was purged with nitrogen, and 10% Pd/C (200 mg, 20 wt %), ethyl acetate (15 ml), and methanol (5 ml) were added. 1,4-cyclohexadiene (0.90 ml, 9.60 mmol) was then added to the mixture, and the solution was allowed to stir at room temperature for about one hour. The reaction mixture was then filtered through a pad of diatomaceous earth and the filter cake was washed with methanol. The filtrate was concentrated in vacuo and the residue purified by column chromatography (silica gel; methylene chloride to 20% methanol/methylene chloride) to afford 456 mg (89% yield) of the desired product. LRMS ([M+H]+)=247.2.

Workup

  1. customwas purged with nitrogen, and 10% Pd/C (200 mg, 20 wt %), ethyl acetate (15 ml), and methanol (5 ml)
  2. additionwere added
  3. filtrationThe reaction mixture was then filtered through a pad of diatomaceous earth
  4. washthe filter cake was washed with methanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by column chromatography (silica gel; methylene chloride to 20% methanol/methylene chloride)

Sources & evidence

ORD record
ord-cab500ab5a86490caef9a39eb4c7cefb
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Linked notes

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