Water → 2-Bromo-6-morpholinopyridine

HRID 1796067Notes

Reaction equation

HRID 1796067 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C(N(CC)CC)C.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.O>CS(C)=O>[Br:8][C:4]1[N:3]=[C:2]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 122742,6-Dibromopyridine

Product 1

HCID 71645992-Bromo-6-morpholinopyridineYield 59.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred solution of 2,6-dibromopyridine (5.0 g, 20.7 mmol), triethylamine (3.0 ml, 21.7 mmol) and morpholine (1.8 g, 20.7 mmol) in dimethylsulfoxide (25 ml) was heated at 85° C. for 4 h. After cooling to ambient temperature the reaction was poured into water. After decanting off the aqueous, the gum was dissolved in dichloromethane, washed with water and saturated brine, then dried over magnesium sulfate, filtered and evaporated in vacuo to give a solid. Purification by chromatography on silica gel eluting with dichloromethane gave 4-(6-bromopyridin-2-yl)morpholine (3.0 g) as a white solid: δH (400 MHz, CDCl3) 3.50 (4H, t, J 5), 3.80 (4H, t, J 5), 6.50 (1H, d, J 8), 6.79 (1H, d, J 8), 7.31 (1H, dd, J 8 and 8); m/z (ES+) 242/244 (M++H).

Workup

  1. customAfter decanting off the aqueous, the gum
  2. dissolutionwas dissolved in dichloromethane
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a solid
  8. customPurification by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-85121705c7b4492dbe17ec0859f1c799
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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