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

HRID 557690Notes

Reaction equation

HRID 557690 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-98992c37d85049a59a2a8afabfff37b4
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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