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With mercaptoethyl alcohol; sepharose bound UDP-glucuronyltransferase; magnesium chloride In ethanol at 37℃; for 4h; Tris-HCl buffer; pH and concentrations varied; enzyme activity;
With mercaptoethyl alcohol; magnesium chloride In ethanol at 37℃; for 4h; Sepharose bound UDP-glucuronyltransferase, Tris-HCl buffer pH 7.5; Yield given;
Preparation of propafenone hydrochloride
Preparation of propafenone hydrochloride 20 g of 2-(2'-hydroxy-3'-propylaminopropoxy)-acetophenone oxalate were dissolved in 450 ml of hot methanol. 16 g of sodium hydroxide, dissolved in 30 ml of distilled water, and 10.6 g of benzaldehyde were added to this solution and the mixture was refluxed for 4 hours. When it had cooled, 2 g of 10% strength Pd/C and 500 ml of methanol were added. The reaction product was hydrogenated under atmospheric pressure (hydrogen absorption: 1,350 ml). The catalyst was filtered off and thoroughly washed with methanol. The filtrate was concentrated. The residue was dissolved in 500 ml of hot 1 N HCl. On cooling, the solution deposited crystals, which were filtered off (crystals I). The filtrate was rendered alkaline and extracted with 3*70 ml of chloroform. The organic phases were combined and concentrated. The residue was brought to pH 2 with 1 N HCl and again concentrated. This new residue was recrystallized from about 250 ml of an 80/20 acetone/methanol mixture. The resulting crystals (II) were filtered off and dried. The yield was 14.9 g=39.4 millimoles (12.1 g of crystals I, and 2.8 g of crystals II), amounting to 67.2% of theory based on 2-(2'-hydroxy-3'-propylaminopropoxy)-acetophenone oxalate employed.
3
[ CAS Unavailable ]
[ 34183-22-7 ]
[ 907997-07-3 ]
Yield
Reaction Conditions
Operation in experiment
35%
With NaOH In methanol at room temp. CuCl2*2H2O in MeOH added to the hydrochloride of the ligand in the same solvent (ratio 1:10), dropwise addition of NaOH; pptn. of crystals after 5 d, crystals filtered, washed with methanol, recrystallized from ethanol, dried over P2O5; elem. anal.;
With NaOH In methanol at room temp., methanolic soln. of hydrochloride of the ligand mixed with soln. of CuCl2*2H2O in the same solvent (ratio 1:1), dropwise additionof NaOH; pptn., crystals filtered, washed with methanol, dried over P2O5; elem. anal.;
With 2,2,6,6-tetramethyl-piperidine; tris(pentafluorophenyl)borate; water-d2 In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; regioselective reaction;
Stage #1: propylamine; 1-(2-(oxiran-2-ylmethoxy)phenyl)-3-phenylpropan-1-one for 4h; Reflux;
Stage #2: With hydrogenchloride In water for 1h; Reflux;
74.5%
Stage #1: propylamine; 1-(2-(oxiran-2-ylmethoxy)phenyl)-3-phenylpropan-1-one at 20 - 50℃; for 6h;
Stage #2: With hydrogenchloride for 1h; Reflux;
5 Example 5
In the reactor, add 248g of 2'-hydroxydihydrochalcone sodium salt,Epichlorohydrin 1L,Heated at 110 for 8 hours,After the reaction is complete,The excess epichlorohydrin was distilled off under reduced pressure, and the residue was cooled to room temperature,Add 600g of n-propylamine and heat to 50 for 6 hours,After the reaction is completed, the excess n-propylamine is distilled off under reduced pressure,Add 1.5L of 10% hydrochloric acid to the remainder and heat to reflux for 1 hour to cool down and crystallize,Filter, filter cake recrystallized with 95% ethanol,Finally getThe target product, propafenone hydrochloride 281g, yield 74.5%.
Multi-step reaction with 3 steps
1.1: 2-Phenylbenzothiazolin; aluminum (III) chloride / toluene / 2 h / 110 °C
1.2: 6 h / 20 - 25 °C
2.1: 8 h / 110 °C
3.1: 6 h / 20 - 50 °C
3.2: 1 h / Reflux
Multi-step reaction with 3 steps
1.1: tris(pentafluorophenyl)borate; triethylsilane; 1,1,1,3',3',3'-hexafluoro-propanol / 1 h / 40 °C
2.1: 4 h / Reflux
3.1: 4 h / Reflux
3.2: 1 h / Reflux
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