Pyrrolidine → 6-(Pyrrolidin-1-yl)pyridine-3-carbaldehyde

HRID 1186355

Reaction equation

HRID 1186355 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[N:10]1([C:2]2[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 164142462-Fluoro-5-formylpyridine

Product 1

HCID 27947756-(Pyrrolidin-1-yl)pyridine-3-carbaldehydeYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

6-Fluoro-3-pyridinecarboxaldehyde (152 mg, 1.22=01) was dissolved in tetrahydrofuran (3.0 mL). To this, pyrrolidine (507 μL, 6.08 mmol) was added under a nitrogen atmosphere at room temperature and the mixture was stirred at the same temperature for 2 hours and successively at 60° C. for 5 hours. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give 6-(pyrrolidin-1-yl)-3-pyridinecarboxaldehyde (181 mg, yield: 84%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2e99f33994db471c9e54fae6db85b2d4
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Linked notes

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