1-Benzyl-4-[N-ethyl-N-(6-fluoro-3-(isopropylamino)-2-pyridinyl)amino]piperidine → 4-[N-Ethyl-N-(6-fluoro-3-(isopropylamino)-2-pyridinyl)amino]piperidine

HRID 361855Notes

Reaction equation

HRID 361855 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:26][CH3:27])[C:15]2[C:20]([NH:21][CH:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=[C:17]([F:25])[N:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[CH2:26]([N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:15]1[C:20]([NH:21][CH:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=[C:17]([F:25])[N:16]=1)[CH3:27]

Participants

4

Reactant 1

HCID 105712191-Benzyl-4-[N-ethyl-N-(6-fluoro-3-(isopropylamino)-2-pyridinyl)amino]piperidine

Product 1

HCID 675760484-[N-Ethyl-N-(6-fluoro-3-(isopropylamino)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

1-Benzyl-4-[N-ethyl-N-(6-fluoro-3-(isopropylamino)-2-pyridinyl)amino]piperidine (EXAMPLE 196, 2.1 g, 5.76 mmol) is dissolved in ethanol (100 ml) and 0.96 g of palladium hydroxide is added. The reaction is placed on a Parr hydrogenator at 40 psi for 12 hr. Then the reaction is filtered through diatomaceous earth, concentrated under reduced pressure, and used without further purification, NMR (300 MHz, CDCl3) 6.93, 6.55, 4.32, 3.51, 3.11, 3.10-2.95, 2.59, 1.77, 1.55, 1.18 and 0.86δ.

Workup

  1. filtrationThen the reaction is filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure
  3. customused without further purification, NMR (300 MHz, CDCl3) 6.93, 6.55, 4.32, 3.51, 3.11, 3.10-2.95, 2.59, 1.77, 1.55, 1.18 and 0

Sources & evidence

ORD record
ord-afba2fbf3f1c412ea197430bde958041
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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