HCID 131711264, compound → 1-{[3-(Morpholin-4-yl)pyrazin-2-yl]oxy}-3-[(propan-2-yl)amino]propan-2-ol

HRID 1764328Notes

Reaction equation

HRID 1764328 reaction equation
Br[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]([O:8][CH2:9][CH:10]([OH:16])[CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])=[N:6][CH:7]=1.[H][H]>CO.[Pd]>[N:17]1([C:4]2[C:5]([O:8][CH2:9][CH:10]([OH:16])[CH2:11][NH:12][CH:13]([CH3:14])[CH3:15])=[N:6][CH:7]=[CH:2][N:3]=2)[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 131711264HCID 131711264, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 713648541-{[3-(Morpholin-4-yl)pyrazin-2-yl]oxy}-3-[(propan-2-yl)amino]propan-2-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7.5 g of 5-bromo-3-morpholinyl-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine are dissolved in 80 ml of methanol and hydrogenated in the presence of 0.4 g of palladium on charcoal (5% strength) at 20°-30° C. under normal pressure. After 10 minutes, the reaction is complete and the calculated amount of hydrogen has been taken up. The catalyst is then filtered off and the filtrate is evaporated in a waterpump vacuum. The residue is partitioned between water and ether. The aqueous 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. 3-Morpholinyl-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine, melting point 74°-76° C., is thus obtained.

Workup

  1. filtrationThe catalyst is then filtered off
  2. customthe filtrate is evaporated in a waterpump vacuum
  3. customThe residue is partitioned between water 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

Sources & evidence

ORD record
ord-55774c3671ed424683d3c685e3e875b7
Source dataset
uspto-grants-1978_09
Patent number
US04115575

Reaction notes

Loading…