Potassium Hydroxide → 5-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

HRID 1532777Notes

Reaction equation

HRID 1532777 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[OH-].[K+].[OH:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 693532,5-DibromopyridineHCID 762881-Pyrrolidineethanol

Product 1

HCID 105881665-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,5-dibromopyridine (15.0 g, 63.3 mmol), powdered KOH (6.39 g, 114 mmol), 1-(2-hydroxyethyl)pyrrolidine (14.58 g, 126.6 mmol), and 18-crown-6 (300 mg, 1.14 mmol) in dry toluene (100 mL) was heated to 70° C. for 1 h. The solution was cooled to room temperature and water and EtOAc were added. The organic layer was washed with water and brine. The solution was dried (MgSO4), filtered, and concentrated in vacuo. Short path distillation (153° C. @0.1 mmHg) provided the title compound as a colorless oil which solidified upon cooling (14.9 g, 87%). 1H NMR (250 MHz, CDCl3): δ8.15 (d, J=2.4 Hz, 1 H), 7.65 (dd, J=2.4, 8.4 Hz, 1 H), 6.67 (d, J=8.4 Hz, 1 H), 4.38 (t, J=5.8 Hz, 2 H), 2.84 (t, J=5.8 Hz, 2 H), 2.62 (m, 4 H), 1.82 (m, 4 H).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialThe solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. distillationShort path distillation (153° C. @0.1 mmHg)

Sources & evidence

ORD record
ord-7ac9ecbaa7c94d5083c927e958a15f2f
Source dataset
uspto-grants-2001_03
Patent number
US06204286B1

Reaction notes

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