U 99363 → 4-[N-Methyl-N-(3-ethoxy-2-pyridinyl)amino]piperidine

HRID 361813

Reaction equation

HRID 361813 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:24])[C:15]2[C:20]([O:21][CH2:22][CH3:23])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:24][N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:15]1[C:20]([O:21][CH2:22][CH3:23])=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 133107U 99363HCID 2723923Ammonium formate

Product 1

HCID 108473684-[N-Methyl-N-(3-ethoxy-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-4-[N-methyl-N-(3-ethoxy-2-pyridinyl)amino]piperidine (EXAMPLE 70, 1.40 g), palladium-on-carbon (10%, 1.4 g) and ammonium formate (813 mg) in methanol (25 ml) is degassed, stirred at 65° for 45 min, cooled to 20°-25°, and filtered to remove catalyst. The filtrate is concentrated under reduced pressure to give the title compound, NMR (CDCl3) 7.83, 6.97, 6.71, 4.02, 3.88, 3.15, 2.88, 2.63, 1.75 and 1.46δ.

Workup

  1. customis degassed
  2. temperaturecooled to 20°-25°
  3. filtrationfiltered
  4. customto remove catalyst
  5. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-4794e628ec764be1bb45fce4998378a0
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Linked notes

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