Ether hydrochloride → HCID 18433004, compound

HRID 2305539Notes

Reaction equation

HRID 2305539 reaction equation
[CH:1](/[C:9]1[CH:18]=[C:17]([NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[ClH:25].CCOCC.[H][H]>CO.[Pd]>[ClH:25].[CH2:1]([C:9]1[CH:18]=[C:17]([NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 10953452Ether hydrochlorideHCID 18432988HCID 18432988, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18433004HCID 18433004, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(E)-(RS)-3-(2-Styryl-quinolin-4-ylamino)-propane-1,2-diol (0.23 g, 0.718 mmol) was dissolved in MeOH (25 ml) and acidified with HCl/Et2O. The reaction mixture was refluxed for 2 hours in the presence of 10% Pd/C (0.02 g) under an atmospheric pressure of hydrogen. The mixture was cooled to room temperature, the catalyst was filtered, and the filtrate was concentrated. Addition of EtOH provided (RS)-3-(2-phenethyl-quinolin-4-ylamino)-propane-1,2-diol hydrochloride (0.075 g, 29%) as a light yellow solid, m. p. 143-145° C., MS: m/e=323.3 (M+H+).

Workup

  1. filtrationthe catalyst was filtered
  2. concentrationthe filtrate was concentrated
  3. additionAddition of EtOH

Sources & evidence

ORD record
ord-078f29017b6e47c0b5b6dc877afec048
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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