2-Chloro-5-nitropyridine → Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate

HRID 1641767Notes

Reaction equation

HRID 1641767 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][O:12][C:13](=[O:21])[CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:11][O:12][C:13](=[O:21])[CH2:14][CH:15]1[CH2:16][CH2:17][N:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 81531DiisopropylethylamineHCID 1515259Methyl 4-piperidineacetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 2-chloro-5-nitropyridine (476 mg, 3.0 mmol) and 4-piperidine acetic acid methyl ester (471 mg, 3.0 mmol) in tetrahydrofuran (10 mL) was added diisopropylethylamine (1.0 mL, 5.74 mmol). The mixture was heated in a microwave at 120° C. for 30 minutes. The mixture was evaporated to dryness and extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The residue was purified using flash chromatography (eluting with ethyl acetate and hexanes) to give (5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid methyl ester as a yellow solid. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. customThe mixture was evaporated to dryness
  2. extractionextracted with ethyl acetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate and solvents
  4. customwere evaporated
  5. customThe residue was purified
  6. washflash chromatography (eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-dc70f4e49d1c497fa6f9cc9459edd7bf
Source dataset
uspto-grants-2012_02
Patent number
US08115011B2

Reaction notes

Loading…