Pyrrolidine → 2-(Pyrrolidin-1-yl)pyridin-4-amine

HRID 2359452Notes

Reaction equation

HRID 2359452 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>>[N:9]1([C:2]2[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 844322-Chloropyridin-4-amine

Product 1

HCID 452591302-(Pyrrolidin-1-yl)pyridin-4-amineYield 79%

Conditions

Temperature
200 °C

Procedure

A mixture of 2-chloro-4-aminopyridine (2.29 g, 17.8 mmol) and pyrrolidine (5.0 mL) was microwave heated at 200° C. for 10 min. After cooling to room temperature, the solid was filtered and washed with dichloromethane (10 mL×3). The filter cake was dissolved in aqueous K2CO3 and extracted with CH2Cl2 (40 mL×3). The combined organic layers were dried over Na2SO4 and concentrated to obtain 2-(pyrrolidin-1-yl)pyridin-4-amine (2.3 g, 79% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was filtered
  3. washwashed with dichloromethane (10 mL×3)
  4. dissolutionThe filter cake was dissolved in aqueous K2CO3
  5. extractionextracted with CH2Cl2 (40 mL×3)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-473bbfc4134d46f7b6013c271becb353
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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