Acetic Acid → 2,4-Diisopropyldibenzo[b,d]furan-1-amine

HRID 1750911Notes

Reaction equation

HRID 1750911 reaction equation
C=C([C:4]1[CH:5]=[C:6]([NH2:20])[C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[C:16]=1[C:17]([CH3:19])=[CH2:18])C.[CH2:21](O)[CH3:22].[C:24](O)(=O)C>[Pt].[Pd]>[CH:21]([C:5]1[CH:4]=[C:16]([CH:17]([CH3:18])[CH3:19])[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]=1[NH2:20])([CH3:22])[CH3:24]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 1184266943,4-Di(prop-1-en-2-yl)dibenzo[b,d]furan-1-amine

Product 1

HCID 584010762,4-Diisopropyldibenzo[b,d]furan-1-amineYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalyst

Procedure

3,4-di(prop-1-en-2-yl)dibenzo[b,d]furan-1-amine (4.8 g, 18.2 mmol), and 5% Pt/C (0.48 g) and 10% Pd/C (0.48 g) were added to a mixture of ethanol (90 mL) and acetic acid (10 mL). Reaction mixture was hydrogenated overnight at 50 psi. Reaction mixture was filtered through a Celite pad and most of the organic solvent was evaporated under vacuum. Crude product was dissolved in ethylacetate and partitioned between 1N NaOH and ethylacetate to get rid of any acetic acid. Organic layer was dried over anhydrous Na2SO4, evaporated under vacuum and purified by flash chromatography over silica gel with 40% DCM/hexanes. Target compound (3.3 g, 68%) was isolated as white crystals.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. filtrationwas filtered through a Celite pad and most of the organic solvent
  4. customwas evaporated under vacuum
  5. dissolutionCrude product was dissolved in ethylacetate
  6. custompartitioned between 1N NaOH and ethylacetate
  7. customto get rid of any acetic acid
  8. dry with materialOrganic layer was dried over anhydrous Na2SO4
  9. customevaporated under vacuum
  10. custompurified by flash chromatography over silica gel with 40% DCM/hexanes

Sources & evidence

ORD record
ord-079e39cb1c954671a313f07472917fda
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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