Formaldehyde → 2-(4-benzhydryl-1-piperazinylmethyl)-6,7-dimethoxy-3,4-dihydro-1(2H)-naphthalenone

HRID 26190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 26190
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.Cl.[CH:17]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C=O.[C:38](=O)([O-])O.[Na+]>O.C(OCC)C.C(O)C>[CH:17]([N:30]1[CH2:35][CH2:34][N:33]([CH2:38][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]2=[O:15])[CH2:32][CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 712FormaldehydeHCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenoneHCID 516892Sodium BicarbonateHCID 441468911-Benzhydrylpiperazinium chloride

Produkt 1

HCID 131795152-(4-benzhydryl-1-piperazinylmethyl)-6,7-dimethoxy-3,4-dihydro-1(2H)-naphthalenone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In 100 ml. of ethanol is dissolved a mixture of 5 g. of 6,7-dimethoxy-3,4-dihydro-1(2H)-naphthalenone, 8 g. of 1-benzhydrylpiperazine hydrochloride and 10 g. of 37% aqueous formalin and the solution is allowed to stand at room temperature overnight, after which time it is heated at 80° C. for 7 hours. To the reaction mixture is added 500 ml. of water and, after shaking with 100 ml. of diethyl ether, the water layer is neutralized with sodium hydrogen carbonate and extracted with chloroform. The extract is dried and distilled under reduced pressure. To the oily residue is added methanol, whereupon 5 g. of 2-(4-benzhydryl-1-piperazinylmethyl)-6,7-dimethoxy-3,4-dihydro-1(2H)-naphthalenone is obtained as colorless crystals melting at 142°-144° C.

Aufarbeitung

  1. additiona mixture of 5 g
  2. additionTo the reaction mixture is added 500 ml
  3. extractionextracted with chloroform
  4. customThe extract is dried
  5. distillationdistilled under reduced pressure
  6. additionTo the oily residue is added methanol

Quellen und Nachweise

ORD-Eintrag
ord-4bf36a752f8c4cf89b8af9f30c002927
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148897

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