Water → 5-Iodo-2-(pyrrolidin-1-yl)pyridine

HRID 1245788Notes

Reaction equation

HRID 1245788 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][N:8]=1.O>CC(N(C)C)=O>[I:13][C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 219144025-Iodo-2-(pyrrolidin-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

Pyrrolidine (1.74 ml) was added to 2-chloro-5-iodopyridine (1 g) in dimethylacetamide (5 ml) and the solution heated at 120° C. for 4 h. After cooling, the reaction mixture was poured into water (60 ml) and the solid precipitate collected by filtration. Recrystallisation from ethyl acetate gave the product as off-white needles (0.33 g); the remaining material was adsorbed onto silica and purified by column chromatography eluting with 0 to 3% ethyl acetate in hexane to give a white solid (0.65 g).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid precipitate collected by filtration
  3. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-e672de39ad4f4659ba6e92cb612c3497
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

Loading…