Diethyl Ether → 5-Morpholinonicotinaldehyde

HRID 1426586Notes

Reaction equation

HRID 1426586 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.C[CH2:15][O:16]CC.C([Li])CCC.CN(C=O)C>CCCCCC>[N:8]1([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([CH:3]=2)[CH:15]=[O:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 467396144-(5-Bromopyridin-3-yl)morpholineHCID 178418339Butyllithium

Product 1

HCID 574778965-MorpholinonicotinaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 4-(5-bromopyridin-3-yl)morpholine (100 mg, 0.0004 mol) in ether (2 mL, 0.02 mol) cooled at −78° C. was treated with 2.5 M n-butyllithium in hexane (0.2 mL) and was stirred for 1 h. To this mixture was added DMF (0.5 mL, 0.006 mol) dropwise. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give 5-morpholin-4-ylnicotinaldehyde (70 mg, 90%) as a crude product. 1H NMR (400 MHz, CDCl3): δ 10.1 (s, 1H), 8.0 (s, 2H), 7.6 (s, 1H), 3.8 (m, 4H), 3.2 (m, 4H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2dd655373fd946be84a1adf440a4e26b
Source dataset
uspto-grants-2015_01
Patent number
US08933086B2

Reaction notes

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