Pyrrolidine → 5-Bromo-2-(pyrrolidin-1-yl)pyridine

HRID 1672239Notes

Reaction equation

HRID 1672239 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>C(O)CCC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 693532,5-Dibromopyridine

Product 1

HCID 164142265-Bromo-2-(pyrrolidin-1-yl)pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 2,5-dibromopyridine (1.60 g, 6.76 mmol) and pyrrolidine (5.64 mL, 67.6 mol) in 1-butanol (10.0 mL) was allowed to stir in a sealed reaction vessel while heating at 75° C. for 16 h. The reaction solvent was evaporated to produce an oily solid which was purified by column chromatography to give 5-bromo-2-(pyrrolidin-1-yl)pyridine (1.50 g, 6.60 mmol, 98%) as a white solid. LCMS (FA): m/z=229.1 (M+H).

Workup

  1. customThe reaction solvent was evaporated
  2. customto produce an oily solid which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7db4e4666da04958bd76522648da563d
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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