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

HRID 1910804Notes

Reaction equation

HRID 1910804 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-0d67fe3a15a14b1d8f68a6508ba63e9f
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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