Morpholine → 1-(6-Bromopyridin-2-yl)-2-morpholin-4-ylethanone

HRID 385796Notes

Reaction equation

HRID 385796 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=1)=[O:4].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[Br:11][C:7]1[N:6]=[C:5]([C:3](=[O:4])[CH2:2][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 534075852-Bromo-1-(6-bromopyridin-2-yl)ethan-1-one

Product 1

HCID 595263201-(6-Bromopyridin-2-yl)-2-morpholin-4-ylethanone

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-1-(6-bromopyridin-2-yl)ethanone (250 mg, 0.90 mmol) in tetrahydrofuran (1 mL) and dimethylformamide (1 mL) was added morpholine (0.18 mL, 2.0 mmol). After 45 minutes, the reaction mixture was diluted with ethyl acetate (30 mL) and washed with saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to afford the title compound.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4c1d8ce65b514d8d8625714bfe11e6e3
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…