1',3',3',6-Tetramethyl-5-nitro-1',2',3',6'-tetrahydro-3,4'-bipyridine → HCID 59405032, compound

HRID 2387999Notes

Reaction equation

HRID 2387999 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 594050051',3',3',6-Tetramethyl-5-nitro-1',2',3',6'-tetrahydro-3,4'-bipyridine

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-39fd5c4285744966b5796f533926e11f
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

Loading…