Allyl Alcohol → 4-{3-[(Prop-2-en-1-yl)oxy]pyrazin-2-yl}morpholine
Reaction equation
Cl[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.[CH2:14]([OH:17])[CH:15]=[CH2:16].[H-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[CH2:14]([O:17][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1)[CH:15]=[CH2:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
120 g of 2-chloro-3-morpholinyl-pyrazine and 70 g of allyl alcohol are dissolved in 640 ml of hexamethylphosphoric acid triamide. 28.8 g of sodium hydride are introduced into this solution over the course of 30 minutes at 0° C. The mixture is then stirred for a further hour at 0° C. and thereafter for 1 hour at 30° C. and 15 hours at room temperature, until the reaction has subsided. The reaction mixture is then poured out onto 2 liters of ice water. After the excess sodium hydride present has been decomposed, the mixture is extracted by shaking with ether. The ether extracts are washed with water until neutral, dried over sodium sulphate and evaporated in a waterpump vacuum. The residue is distilled in a high vacuum. 2-Allyloxy-3-morpholinyl-pyrazine, boiling point 105°-106° C./0.03 mm Hg, is thus obtained.
Workup
- custom15 hours
- customat room temperature
- extractionthe mixture is extracted
- stirringby shaking with ether
- washThe ether extracts are washed with water until neutral,
- dry with materialdried over sodium sulphate
- customevaporated in a waterpump vacuum
- distillationThe residue is distilled in a high vacuum
Sources & evidence
- ORD record
- ord-4a7d77d451de4beb854b52acf32445a8
- Source dataset
- uspto-grants-1980_03
- Patent number
- US04195090
Reaction notes
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