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Sodium Bicarbonate → Ethyl 4-[2-[1-(8-chloro-3-phthalazinyl)-4-piperidinyl]ethoxy]benzoate monohydrochloride

HRID 484514
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 484514
[Cl:1][N:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[CH:9]2)=[CH:4][NH:3]1.[NH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][O:21][C:22]2[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=2)[CH2:15][CH2:14]1.C(=O)([O-])O.[Na+]>C(O)C>[ClH:1].[Cl:12][C:6]1[C:5]2[C:10](=[CH:11][N:2]([N:13]3[CH2:14][CH2:15][CH:16]([CH2:19][CH2:20][O:21][C:22]4[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:31][CH:32]=4)[CH2:17][CH2:18]3)[NH:3][CH:4]=2)[CH:9]=[CH:8][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 14989200Ethyl 4-[2-(4-piperidinyl)ethoxy]benzoateHCID 197482793,8-Dichlorophthalazine

Produkt 1

HCID 19748240Ethyl 4-[2-[1-(8-chloro-3-phthalazinyl)-4-piperidinyl]ethoxy]benzoate monohydrochlorideAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702Ethanol
Lösungsmittel

Versuchsvorschrift

A mixture of 4 parts of 3,8-dichlorophthalazine, 4.2 parts of ethyl 4-[2-(4-piperidinyl) ethoxy]benzoate, 4 parts of sodium hydrogen carbonate and 120 parts of ethanol was stirred and refluxed overnight. After evaporation, the residue was taken up in water and dichloromethane. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane and methanol (98.2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off, washed with 2-propanol and 2,2'-oxybispropane and dried at 50° C., yielding 3.3 parts (46.2%) of ethyl 4-[2-[1-(8-chloro-3-phthalazinyl)-4-piperidinyl]ethoxy]benzoate monohydrochloride; mp. 172.4° C. (comp. 86).

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customAfter evaporation
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. washwashed with 2-propanol and 2,2'-oxybispropane
  11. customdried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-c90eac6e5ee74bae8841f9bf41271435
Quelldatensatz
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05231184

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