Reaktion #334279

Reaktionsgleichung

triethylamine

N-hydroxy-3,3-diphenylpropylamine

hydrogen chloride

methyl 2-bromoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate

→

methyl N-(3,3-diphenylpropyl)-N-hydroxy-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate

Lösungsmittel

dimethylformamide

acetone

water

diethyl ether

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then maintained in a nitrogen atmosphere
2. 2
   TemperaturAfter cooling
3. 3
   Extraktionextracted with a diethyl ether
4. 4
   WaschenThe organic layer was washed many times with water
5. 5
   Sonstigedried
6. 6
   SonstigeThe solvent was evaporated off in vacuo
7. 7
   SonstigeThe oily residue obtained
8. 8
   Sonstigewas purified first by chromatography on a silica gel column with ethyl acetate gradient in toluene
9. 9
   workup.ADDITIONon a silica gel column containing ammonia at 5.5% by weight with about 6 N methanolic ammonia gradient in chloroform
10. 10
    SonstigeThe solid thus obtained
11. 11
    FiltrationThe hydrochloride hemihydrate of the title compound was filtered off
12. 12
    Waschenwashed with isopropanol
13. 13
    Sonstigedried at 100° C.

Vorschrift

3 ml of triethylamine were added to a solution of 2.40 g of N-hydroxy-3,3-diphenylpropylamine in 17 ml of dimethylformamide. 4.39 g of methyl 2-bromoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate were added to the mixture. The mixture was then maintained in a nitrogen atmosphere and heated for 160 minutes at 105° C. After cooling, the mixture was poured into water and extracted with a diethyl ether: ethyl acetate mixture. The organic layer was washed many times with water and then dried. The solvent was evaporated off in vacuo. The oily residue obtained was purified first by chromatography on a silica gel column with ethyl acetate gradient in toluene and then on a silica gel column containing ammonia at 5.5% by weight with about 6 N methanolic ammonia gradient in chloroform. The solid thus obtained was dissolved in a 2:1 by volume acetone: diethyl ether mixture and hydrogen chloride in diethyl ether was added. The hydrochloride hemihydrate of the title compound was filtered off, washed with isopropanol and dried at 100° C. and 0.5 mmHg for 1 hour. Yield 1.51 g, m.p. 100°-105° C.

Quelle