Picolyl chloride hydrochloride → 2-(Pyrrolidin-1-ylmethyl)pyridine

HRID 465049Notes

Reaction equation

HRID 465049 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)C>[N:10]1([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 23392Picolyl chloride hydrochlorideHCID 31268Pyrrolidine

Product 1

HCID 14390642-(Pyrrolidin-1-ylmethyl)pyridineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

With stirring and external cooling with ice, a solution of 2-(chloromethyl)pyridine hydrochloride (100 g, 0.61 mol) in 95% ethanol (600 ml) is added dropwise to pyrrolidine (500 ml, 426 g, 5.99 mol) and the resulting mixture is heated to 90° C. for 1 hour. After cooling, the mixture is suction filtered, the filter residue is thoroughly washed with ether, the filtrate is concentrated in vacuo and the residue is made strongly alkaline with 40% potassium hydroxide solution. It is extracted exhaustively with ether, the extracts obtained are freed from solvent and the remaining residue is distilled in vacuo. The desired compound (93.0 g) is obtained. Boiling point 19 mm Hg 118°-121° C.

Workup

  1. temperatureexternal cooling with ice
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. washthe filter residue is thoroughly washed with ether
  5. concentrationthe filtrate is concentrated in vacuo
  6. extractionIt is extracted exhaustively with ether
  7. customthe extracts obtained
  8. distillationthe remaining residue is distilled in vacuo

Sources & evidence

ORD record
ord-c9b617fdb4b34780b4d12be45d8d6389
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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