o-CRESYL GLYCIDYL ETHER → HCID 21333213, compound

HRID 2399163Notes

Reaction equation

HRID 2399163 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[O:8][CH2:7]1.[CH3:13][C:14]1[C:19]([O:20][CH2:21][CH2:22][NH2:23])=[N:18][CH:17]=[CH:16][N:15]=1>C(O)(C)C>[CH3:13][C:14]1[C:19]([O:20][CH2:21][CH2:22][NH:23][CH2:7][CH:6]([OH:8])[CH2:5][O:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=2[CH3:1])=[N:18][CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 16640o-CRESYL GLYCIDYL ETHER2×HCID 21333189HCID 21333189, compound

Product 1

HCID 21333213HCID 21333213, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4.92 g of 1-(o-methyl-phenoxy)-2,3-epoxypropane and 4.59 g of 2-methyl-3-(2-amino-ethoxy)pyrazine in 150 ml of isopropanol is stirred for 24 hours at about 20° C. and thereafter a further 1.47 g of 1-(o-methyl-phenoxy)-2,3-epoxy-propane are added. After standing for a further 24 hours at about 20° C., the reaction mixture is evaporated under a waterpump vacuum, the residue is dissolved in ether, the ether solution is extracted by shaking with 2 N hydrochloric acid and the combined hydrochloric acid extracts are rendered alkaline with sodium hydroxide solution and extracted by shaking with ether. The combined ether extracts are washed with water, dried over sodium sulphate and evaporated under a waterpump vacuum. The residue crystallises from methylene chloride/petroleum ether, giving 1-[2-(2-methyl-3-pyrazinyloxy)-ethyl-amino]-3-(2-methyl-phenoxy)-2-propanol; melting point 82°-84° C. The acid fumarate prepared with the calculated amount of fumaric acid crystallises from isopropanol, melting point 140°-141° C.

Workup

  1. customthe reaction mixture is evaporated under a waterpump vacuum
  2. dissolutionthe residue is dissolved in ether
  3. extractionthe ether solution is extracted
  4. extractionextracted
  5. stirringby shaking with ether
  6. washThe combined ether extracts are washed with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated under a waterpump vacuum
  9. customThe residue crystallises from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-6ce63723206e4b1c9dfbc701e5d03d9d
Source dataset
uspto-grants-1977_05
Patent number
US04027027

Reaction notes

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