HCID 22141145, compound → HCID 22141195, compound

HRID 428930Notes

Reaction equation

HRID 428930 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[CH:16][C:17]([N+:21]([O-])=O)=[C:18]([NH2:20])[CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(O)C.[Pd]>[NH2:20][C:18]1[CH:19]=[C:14]([C:10]2([CH3:13])[CH:9]3[CH:11]2[CH2:12][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8]3)[CH:15]=[CH:16][C:17]=1[NH2:21]

Participants

4

Reactant 1

HCID 22141145HCID 22141145, compound

Product 1

HCID 22141195HCID 22141195, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)-2-nitrophenylarnine (Preparation 47, 360 mg, 1.14 mmol) in ethanol (15 ml) was added 10% palladium on carbon (50 mg). The mixture was placed under an atmosphere of hydrogen (50 psi, 345 kPa) and heated at 50° C. for 16 hours. The mixture was then cooled and filtered through Celite™, washing with ethanol. The filtrate was concentrated in vacuo to give the crude title compound (328 mg, 100%) as a yellow oil which was used without further purification.

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered through Celite™
  3. washwashing with ethanol
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ae43170307fb4e72882520202e88b7f8
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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