Hydrochloric Acid → 2-(3,3,4,4-Tetramethylcyclopentyl)phenylamine

HRID 2218818Notes

Reaction equation

HRID 2218818 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH2:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[CH:11]=1)([O-])=O.Cl.C(OCC)(=O)C>[Pd].CO>[CH3:17][C:12]1([CH3:18])[C:13]([CH3:15])([CH3:16])[CH2:14][CH:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])[CH2:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 231417801-Nitro-2-(3,3,4,4-tetramethylcyclopent-1-enyl)benzene

Product 1

HCID 231427522-(3,3,4,4-Tetramethylcyclopentyl)phenylamineYield 74.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 1-nitro-2-(3,3,4,4-tetramethylcyclopent-1-enyl)benzene (450 mg, 1.83 mmol) produced in Example (54b), 10% palladium on carbon (200 mg, wet) and methanol (40 mL) was stirred for 3 hours and 30 minutes at atmospheric pressure and room temperature under a hydrogen atmosphere. The reaction mixture was filtered, 10% palladium on carbon (200 mg, hydrous) and a 4N solution of hydrogen chloride in ethyl acetate (0.915 mL, 3.66 mmol) were added to the filtrate, and then stirring was continued for 13 hours and 30 minutes at room temperature and atmospheric pressure under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 295 mg of the title compound as a brown oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. stirringstirring
  3. waitwas continued for 13 hours and 30 minutes at room temperature
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e4909ebb02f6400f839b65e4226d7c8e
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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