Water → 4-[(6-Chloropyridin-3-yl)methyl]morpholine

HRID 37856Notes

Reaction equation

HRID 37856 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[N:13][CH:14]=1.O>C(Cl)(Cl)(Cl)Cl>[Cl:15][C:12]1[N:13]=[CH:14][C:9]([CH2:8][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 64246615-(Bromomethyl)-2-chloropyridine

Product 1

HCID 36140454-[(6-Chloropyridin-3-yl)methyl]morpholineYield 21%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Morpholine (7.0 g, 8.8 mmol) was added to the solution of 5-bromomethyl-2-chloro-pyridine in carbon tetrachloride (20 mL) and stirred at room temperature for 6 h. Water was added to the reaction mixture and the separated organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product. Purification by column chromatography using silica gel (60-120 mesh) and ethyl acetate as eluent afforded 4-(6-chloro-pyridin-3-yl-methyl)-morpholine (1.2 g, 21%) as a brown oily liquid.

Workup

  1. washthe separated organic layer was washed with water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford the crude product
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-46dd1aa8068b43059234b7dbbed4daae
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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