Morpholine → 4-(5-Bromopyrazin-2-yl)morpholine

HRID 1157809Notes

Reaction equation

HRID 1157809 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[Br:9][C:10]1[C:15](Br)=[N:14][CH:13]=[CH:12][N:11]=1>C1COCC1>[Br:9][C:10]1[N:11]=[CH:12][C:13]([N:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 24758Sodium hydrideHCID 138675722,3-Dibromopyrazine

Product 1

HCID 457874804-(5-Bromopyrazin-2-yl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To sodium hydride (0.20 g) taken in THF (15 ml), morpholine (0.735 ml) was added under nitrogen, at 0° C. The reaction mixture stirred for about 15 minutes, then 2,3-dibromopyrazine (2 g) dissolved in dry THF (15 ml) was added. The reaction mixture was allowed to stir at reflux conditions for overnight. The reaction mixture was quenched with water (5 ml), and volatiles were removed under vacuum. The resulting crude mass was purified by column chromatography to afford pure 4-(5-bromopyrazin-2-yl)morpholine.

Workup

  1. additionwas added
  2. stirringto stir
  3. temperatureat reflux conditions for overnight
  4. customThe reaction mixture was quenched with water (5 ml), and volatiles
  5. customwere removed under vacuum
  6. customThe resulting crude mass was purified by column chromatography

Sources & evidence

ORD record
ord-e745a98e4fa24b41968cda4677f6a632
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

Loading…