Sodium hydride → HCID 20438894, compound

HRID 1758720Notes

Reaction equation

HRID 1758720 reaction equation
C1(C2[N:11]([CH:12]([CH3:14])[CH3:13])[CH2:10][CH:9]([CH2:15][OH:16])[O:8]2)C=CC=CC=1.[H-].[Na+].Cl[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27]C2CCCCO2)[N:21]=1>CN(C)C=O>[CH:12]([NH:11][CH2:10][CH:9]([OH:8])[CH2:15][O:16][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[N:21]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 125661982-Phenyl-3-isopropyl-5-hydroxymethyloxazolidineHCID 20438889HCID 20438889, compound

Product 1

HCID 20438894HCID 20438894, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

22.2 g of 2-phenyl-3-isopropyl-5-hydroxymethyloxazolidine was dissolved in 130 ml of anhydrous dimethyl formamide, and with stirring, 50% sodium hydride was added. To the resulting solution was added a solution of 22.75 g of 2-chloro-6-(tetrahydro-2-pyranyloxy)methylpyridine in 250 ml of anhydrous dimethyl formamide. The mixture was stirred at 80° C. for 1 hour. After the reaction, the solvent was distilled off under reduced pressure, and 500 ml of 10% hydrochloric acid was added. The mixture was stirred at 80° C. for 20 minutes. The reaction solution was evaporated to dryness under reduced pressure to afford 10 g (yield 41.6%) of 1-isopropylamino-3-(6-hydroxymethyl-2-pyridyloxy)-2-propanol.

Workup

  1. stirringThe mixture was stirred at 80° C. for 1 hour
  2. customAfter the reaction
  3. distillationthe solvent was distilled off under reduced pressure, and 500 ml of 10% hydrochloric acid
  4. additionwas added
  5. stirringThe mixture was stirred at 80° C. for 20 minutes
  6. customThe reaction solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-16bfe9d2525a4102a6787870df02b683
Source dataset
uspto-grants-1983_02
Patent number
US04374840

Reaction notes

Loading…