Sulfuric Acid → 2-(3-Cyclopropylcyclobutyl)phenylamine

HRID 2240484Notes

Reaction equation

HRID 2240484 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1(O)[CH2:11][CH:10]([CH:12]2[CH2:14][CH2:13]2)[CH2:9]1.S(=O)(=O)(O)O>C(O)C.[Pd]>[CH:12]1([CH:10]2[CH2:11][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH2:1])[CH2:9]2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 685847901-(2-Aminophenyl)-3-cyclopropylcyclobutanol

Product 1

HCID 685852852-(3-Cyclopropylcyclobutyl)phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.22 g (0.006 mol) 1-(2-aminophenyl)-3-cyclopropylcyclobutanol (prepared as described in Example 9) was dissolved in 40 ml of ethanol, 1.72 g sulphuric acid (96%) were added and after addition of 250 mg of 10% Pd on charcoal, the mixture was hydrogenated for 5.5 hours at room temperature. After removal of the catalyst, ethanol was distilled off in a water jet vacuum and the residue purified by flash chromatography over silica gel (eluent: hexane/ethyl acetate 5:1). Yield: 0.94 g (82% of theory) of a cis/trans mixture of 2-(3-cyclopropylcyclobutyl)phenylamine in the form of a yellow oil (MS: M+-peak of 187).

Workup

  1. customAfter removal of the catalyst, ethanol
  2. distillationwas distilled off in a water jet vacuum
  3. customthe residue purified by flash chromatography over silica gel (eluent: hexane/ethyl acetate 5:1)
  4. additionYield: 0.94 g (82% of theory) of a cis/trans mixture of 2-(3-cyclopropylcyclobutyl)phenylamine in the form of a yellow oil (MS: M+-peak of 187)

Sources & evidence

ORD record
ord-acf959dbb3094498a3f7ddd37cafb187
Source dataset
uspto-grants-2010_05
Patent number
US07723371B2

Reaction notes

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