Hydrochloric Acid → 2-[4-(1,2,3,4-Tetrahydro-8-methoxy-2-naphthalenyl)-1-piperazinyl]pyrimidine

HRID 231311

Reaktionsgleichung

Reaktionsgleichung von HRID 231311
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C:10](=O)[CH2:9][CH2:8]2.Cl.Cl.[N:16]1[CH:21]=[CH:20][CH:19]=[N:18][C:17]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(C(C)C)CC)(C)C.Cl.C([BH3-])#N.C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:25]1[CH2:26][CH2:27][N:22]([C:17]3[N:16]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:23][CH2:24]1)[CH2:9][CH2:8]2

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 81531DiisopropylethylamineHCID 2724287Tetrabutylammonium (cyano-C)trihydroborateHCID 41360218-Methoxy-2-tetraloneHCID 116802722-Piperazinylpyrimidine dihydrochloride

Produkt 1

HCID 144799982-[4-(1,2,3,4-Tetrahydro-8-methoxy-2-naphthalenyl)-1-piperazinyl]pyrimidineAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

8-Methoxy-2-tetralone (3.5 g, 20 mmole), 1-(2-pyrimidinyl) piperazine dihydrochloride (4.6 g, 20 mmole), 0.38 g of p-toluenesulfonic acid and 3.48 ml of diisopropylethylamine were combined in 200 ml of toluene and the mixture refluxed under N2 for three days with water removal via a Dean-Stark trap. After the reaction had cooled, 10.5 ml of 4 N isopropanolic HCl was added, followed in portions by 5.93 g of tetra-n-butyl ammonium cyanoborohydride. The mixture was refluxed under N2 for one hour and the solvent removed in vacuum. The residue was redissolved in 300 ml of CHCl3, washed with saturated NaHCO3 solution, dried over MgSO4, filtered, and evaporated in vacuum. The crude product was column chromatographed on 75 g of silica gel employing chloroform as the eluent and the relevant fractions were combined and concentrated in vacuum. The crude title compound was crystallized from 50 ml of isopropanol with addition of 4 N isopropanolic HCl to obtain 2.0 g of the title compound as the monohydrochloride. A second crystallization from isopropanol gave 1.3 g of monohydrochloride, m.p. 273°-276° C. (d).

Aufarbeitung

  1. temperatureAfter the reaction had cooled
  2. temperatureThe mixture was refluxed under N2 for one hour
  3. customthe solvent removed in vacuum
  4. dissolutionThe residue was redissolved in 300 ml of CHCl3
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuum
  9. customchromatographed on 75 g of silica gel
  10. concentrationconcentrated in vacuum
  11. customThe crude title compound was crystallized from 50 ml of isopropanol with addition of 4 N isopropanolic HCl

Quellen und Nachweise

ORD-Eintrag
ord-6f63797e1c154b1e9e37ab59f6d766ab
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845221

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