Ethanol → Tert-butyl 4-(4-amino-2-methoxyphenyl)piperidine-1-carboxylate

HRID 869246Notes

Reaction equation

HRID 869246 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=1.C(O)C>[Pd].C1COCC1>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]2)=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 66642865tert-butyl 4-(2-methoxy-4-nitrophenyl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 66642900Tert-butyl 4-(4-amino-2-methoxyphenyl)piperidine-1-carboxylateYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 4-(2-methoxy-4-nitrophenyl)-3,6-dihydropyridine-1(2H)-carboxylate (Preparation Example 412) (2.21 g), ethanol (40 mL) and THF (20 mL), 10% palladium on carbon (1.0 g) was added and stirred at room temperature for 3 hours under a hydrogen atmosphere at normal pressure. After filtration through celite, the filtrate was distilled off under reduced pressure to give tert-butyl 4-(4-amino-2-methoxy-phenyl)piperidine-1-carboxylate (1.97 g) as a gray solid.

Workup

  1. additionwas added
  2. filtrationAfter filtration through celite
  3. distillationthe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7f75a7bde410467082d2d2ffb377a0bf
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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