Isopropylamine → 1-[(3-Chloropyrazin-2-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

HRID 1701739Notes

Reaction equation

HRID 1701739 reaction equation
Br[CH2:2][CH:3]([OH:13])[CH2:4][O:5][C:6]1[C:11]([Cl:12])=[N:10][CH:9]=[CH:8][N:7]=1.[CH:14]([NH2:17])([CH3:16])[CH3:15]>CO>[Cl:12][C:11]1[C:6]([O:5][CH2:4][CH:3]([OH:13])[CH2:2][NH:17][CH:14]([CH3:16])[CH3:15])=[N:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 204834011-Bromo-3-[(3-chloropyrazin-2-yl)oxy]propan-2-ol

Product 1

HCID 204834181-[(3-Chloropyrazin-2-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

53 g of 2-(3'-bromo-2'-hydroxy-propoxy)-3-chloropyrazine and 59 g of isopropylamine in 500 ml of methanol are boiled for 15 hours under reflux. The reaction mixture is then evaporated in a waterpump vacuum. The residue is partitioned between 2 N hydrochloric acid and ether. The hydrochloric acid phase is rendered alkaline with concentrated sodium hydroxide solution and extracted by shaking with ether. The ether extracts are washed with water, dried over sodium sulphate and evaporated in a waterpump vacuum. The residue crystallises from ether. 3-Chloro-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine, melting point 99°-100° C., is thus obtained.

Workup

  1. temperatureunder reflux
  2. customThe reaction mixture is then evaporated in a waterpump vacuum
  3. customThe residue is partitioned between 2 N hydrochloric acid and ether
  4. extractionextracted
  5. washThe ether extracts are washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated in a waterpump vacuum
  8. customThe residue crystallises from ether

Sources & evidence

ORD record
ord-dd3b342910b94f97813d6cc854fea4c2
Source dataset
uspto-grants-1980_03
Patent number
US04195090

Reaction notes

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