Water → 6-(Pyrrolidin-1-yl)pyridin-2-amine

HRID 2359453Notes

Reaction equation

HRID 2359453 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.O>CS(C)=O>[N:15]1([C:6]2[N:5]=[C:4]([NH2:8])[CH:3]=[CH:2][CH:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 567666396-(Pyrrolidin-1-yl)pyridin-2-amineYield 37%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 4-chloro-2-aminopyridine (19.3 g, 0.150 mol), K2CO3 (41.7 g, 0.30 mol) and pyrrolidine (32.0 g, 0.45 mol) in DMSO (150 mL) was stirred at 190° C. for 10 hours. After cooling to room temperature, water (300 mL) was added and extracted with ethyl acetate (150 mL×4). The combined organic layers were washed with water (25 mL×3), dried over Na2SO4 and concentrated in vacuo, the residue was purified by silica gel chromatography (10:1 ethyl acetate/petroleum ether) to obtain 6-(pyrrolidin-1-yl)pyridin-2-amine (9.0 g, 37% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (150 mL×4)
  3. washThe combined organic layers were washed with water (25 mL×3)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (10:1 ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-ab6ebf7b1b8344fca4c699a1ad790a72
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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