Morpholine → 4-(6-Chloropyrazin-2-yl)morpholine

HRID 594040Notes

Reaction equation

HRID 594040 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>C(#N)C>[Cl:8][C:4]1[N:3]=[C:2]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 785042,6-Dichloropyrazine

Product 1

HCID 263702094-(6-Chloropyrazin-2-yl)morpholineYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,6-dichloropyrazine (1.0 equiv.) in acetonitrile (0.3 M) was added morpholine (3.5 equiv.) and the reaction was stirred at room temperature for 20 h. The resulting precipitate was filtered off and the filtrate was concentrated under vacuo. The crude material was partitioned between water and ethyl acetate, the organic phase was dried with sodium sulfate, filtered and concentrated to afford 4-(6-chloropyrazin-2-yl)morpholine in 75% yield. LCMS m/z (M+H)=200.0, Rt=0.61 min.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. concentrationthe filtrate was concentrated under vacuo
  3. customThe crude material was partitioned between water and ethyl acetate
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c51e1727ec4b4dc1822427928e96b29e
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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