4-[4-(2-acetylaminopropyl)phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-[4-(2-Acetylaminopropyl)phenyl]piperidine-1-carboxylic acid tert-butyl ester

HRID 1470718Notes

Reaction equation

HRID 1470718 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 671254354-[4-(2-acetylaminopropyl)phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 671254804-[4-(2-Acetylaminopropyl)phenyl]piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.20 g (6.14 mmol) 4-[4-(2-Acetylamino-propyl)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (VI.1) in 100 mL methanol are hydrogenated (50 psi) for 7.0 h at rt using 250 mg palladium on charcoal(10%). After that time, the catalyst is filtered off and the solvent is evaporated to yield the desired product.

Workup

  1. customfor 7.0 h
  2. customat rt
  3. filtrationAfter that time, the catalyst is filtered off
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-92191d287f5a4b0e9b3162a23e44db9c
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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