Tetrahydrofuran → tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

HRID 1064360Notes

Reaction equation

HRID 1064360 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.O1CCCC1>CO.[Pd].[H][H]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 15751429Tert-butyl 4-(3-nitrophenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylateYield 99.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a solution of 2.54 g of tert-butyl 1,2,3,6-tetrahydro-4-(3-nitrophenyl)pyridine-1-carboxylate (which was prepared by the method as described in Synthesis, 1991, 993-995) in 20 ml of methanol, 250 mg of 10% palladium-on-carbon catalyst was added, and stirred for an hour in hydrogen atmosphere at ambient temperature and pressure. After addition of 20 ml of tetrahydrofuran to the reaction liquid, the liquid was filtered with Celite. Distilling the solvent off under reduced pressure, 2.30 g of the title compound was obtained.

Workup

  1. customto the reaction liquid
  2. filtrationthe liquid was filtered with Celite
  3. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-7da3d97eb32140399b67bb85cf6efebc
Source dataset
uspto-grants-2005_11
Patent number
US06969712B2

Reaction notes

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