tert-Butyl 4-(3-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

HRID 2085403Notes

Reaction equation

HRID 2085403 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1>C(O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22049056tert-Butyl 4-(3-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylateYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.10 g of tert-butyl 4-(3-aminophenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate (11.3 mmol) and 1.0 g of 10% Pd/C in 200 mL of ethanol was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane: methanol 95:5 with 1% isopropylamine added to protect the BOC group from hydrolysis) to give 2.63 g of the desired product (84%).

Workup

  1. customwas hydrogenated at room temperature
  2. customfor 2 days
  3. filtrationThe reaction mixture was filtered
  4. washwashed with ethanol
  5. concentrationThe combined ethanol extracts were concentrated in vacuo
  6. customthe residue was chromatographed on silica (dichloromethane: methanol 95:5 with 1% isopropylamine
  7. additionadded
  8. customfrom hydrolysis)

Sources & evidence

ORD record
ord-da33508cd3214d978cdd0018a9e0c175
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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