Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate → Methyl [1-(5-aminopyridin-2-yl)piperidine-4-yl]acetate

HRID 1713819Notes

Reaction equation

HRID 1713819 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:11]2)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 47357980Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate

Product 1

HCID 59464078Methyl [1-(5-aminopyridin-2-yl)piperidine-4-yl]acetateYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate (710 mg, 2.60 mmol) in EtOH (26 mL) was treated with 10% Pd on charcoal (71 mg), and stirred vigorously under an atmosphere of hydrogen for 4 h. The reaction mixture was filtered through diatomaceous earth and the filtrate was evaporated to dryness to give the title compound (556 mg, 70%) as an oil; 1H NMR δ 1.12-1.27 (2H, m), 1.67 (2H, d), 1.75-1.89 (1H, m), 2.25 (2H, d), 2.56 (2H, t), 3.33 (2H, s), 3.58 (3H, s), 4.52 (2H, s), 6.61 (1H, d), 6.86-6.93 (1H, m), 7.58 (1H, d); MS m/e MH+ 250.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-97b9017391684f28993846c1aa9fbcfd
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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