HCID 59405005, compound → HCID 59405032, compound

HRID 1892198Notes

Reaction equation

HRID 1892198 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[N:10][C:11]([CH3:17])=[C:12]([N+:14]([O-])=O)[CH:13]=2)[C:4]([CH3:19])([CH3:18])[CH2:3]1>CO.[OH-].[Pd+2].[OH-]>[CH3:17][C:11]1[C:12]([NH2:14])=[CH:13][C:8]([CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][C:4]2([CH3:19])[CH3:18])=[CH:9][N:10]=1

Participants

4

Reactant 1

HCID 59405005HCID 59405005, compound

Product 1

HCID 59405032HCID 59405032, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1′,3′,3′,6-tetramethyl-5-nitro-1′,2′,3′,6′-tetrahydro-3,4′-bipyridine (0.912 g, 3.49 mmol) in MeOH (70 mL) was added palladium hydroxide (20 wt. % Pd (dry basis) on carbon, 808 mg). The reaction mixture was flushed with hydrogen gas and allowed to stir at rt overnight under an atmosphere of hydrogen. The reaction mixture was filtered through a Celite® pad and washed with MeOH. The filtrate was concentrated to give 2-methyl-5-(1,3,3-trimethylpiperidin-4-yl)pyridine-3-amine (0.814 g, 100%). LCMS (FA): Rt=0.24 min, m/z=234.4 (M+H).

Workup

  1. customThe reaction mixture was flushed with hydrogen gas
  2. filtrationThe reaction mixture was filtered through a Celite® pad
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9f3c6e488e2c4d429bc1f6430b30b723
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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