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

HRID 1270010

Reaktionsgleichung

Reaktionsgleichung von HRID 1270010
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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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): δ 8.15 (d, J=2.4 Hz, 1H), 7.65 (dd, J=2.4, 8.4 Hz, 1H), 6.67 (d, J=8.4 Hz, 1H), 4.38 (t, J=5.8 Hz, 2H), 2.84 (t, J=5.8 Hz, 2H), 2.62 (m, 4H), 1.82 (m, 4H).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-12d1c0f7b89c4774be1ebbf9970b62dd
Quelldatensatz
uspto-grants-2007_04
Patentnummer
USRE039558E1

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