Reaktion #2194072

Reaktionsgleichung

sulfuric acid

dimethylamine

1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine sulfate

formaldehyde

dimethylamine

sulfuric acid

1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine

sulfuric acid

sodium hydroxide

→

1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine sulfate

1,4,5,6-tetrahydro-4-(3-methoxyphenyl)-N,N,I-trimethyl-4-propyl-3-pyridinemethanamine

Lösungsmittel

water

water

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile maintaining the pH of the reaction mixture between 3-3.5
2. 2
   ExtraktionThe resulting suspension was extracted twice with 50 ml portions of hexane
3. 3
   Waschenwashed five times with 50 ml portions of water, one time with a 50 ml portion of saturated sodium chloride
4. 4
   Trocknendried over 5 g of anhydrous sodium sulfate
5. 5
   SonstigeEvaporation of the solvent under reduced pressure

Vorschrift

To a solution of 10 g (0.123 mol) of 37% aqueous formaldehyde and 15 g (0.133 mol) of 40% aqueous dimethylamine in 100 ml of water was added enough concentrated sulfuric acid so as to adjust the pH of the reaction mixture to 3-4. A solution of 25 g (0.0867 mol) of 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine sulfate in approximately 40 ml of water was added and the pH adjusted to 3-3.5, if necessary, by the addition of sulfuric acid or 40% aqueous dimethylamine. The 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine sulfate solution was prepared by the extraction of 25 g of 1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1-methyl-4-propylpyridine in 50 ml of hexane with a total of about 40 ml of 2.5N sulfuric acid. The mixture was stirred at approximately 65°-70° C. for 2 hours while maintaining the pH of the reaction mixture between 3-3.5. The solution was cooled to 30° C. and added to 100 ml of 25% sodium hydroxide. The resulting suspension was extracted twice with 50 ml portions of hexane. The organic extracts were combined and washed five times with 50 ml portions of water, one time with a 50 ml portion of saturated sodium chloride and dried over 5 g of anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure afforded 28.4 g of crude 1,4,5,6-tetrahydro-4-(3-methoxyphenyl)-N,N,I-trimethyl-4-propyl-3-pyridinemethanamine as an oil. Purity 85% by NMR. Yield 92.3%. m/e Theory calculated for C19HY30N2O: 302.2376; Found 302.2394. NMR: (CDCl3) δ0.92 (3H,t), 2.17 (6H,s), 2.63 (3H,s), 3.78 (3H,s), 6.10 (1H,s), 6.7-7.2 (4H,m,aryl). 13C NMR: (CDCl3) δ14.92(q), 18.11(t), 36.32(t), 40.16(t), 43.03(q), 43.47(s), 45.80(q), 46.28(t), 55.11(q), 60.80(t), 109.02(s), 110.32(d), 114.33(d), 120.68(d), 128.52(d), 136.64(d), 151.65(s), 159.24(s).

Quelle