Hydrochloric Acid → 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[3-(1-methylethyl)aminopropyl]phenoxy]ethyl]piperazine trihydrochloride

HRID 2418004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2418004
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26]Cl)[CH2:21][CH2:20]3)[C:4]=2[CH:3]=1.[CH3:28][CH:29]([NH:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1)[CH3:30].[OH-].[Na+].[ClH:44]>CS(C)=O.C(OCC)(=O)C.C(Cl)(Cl)Cl>[ClH:1].[ClH:44].[ClH:1].[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][O:41][C:38]4[CH:39]=[CH:40][C:35]([CH2:34][CH2:33][CH2:32][NH:31][CH:29]([CH3:28])[CH3:30])=[CH:36][CH:37]=4)[CH2:23][CH2:24]3)[C:4]=2[CH:3]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 52754552-Chloro-10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]phenothiazineHCID 204469574-[3-(1-Methylethyl)aminopropyl]phenol

Produkt 1

HCID 133384731-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[3-(1-methylethyl)aminopropyl]phenoxy]ethyl]piperazine trihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Using the conditions described above in method A, 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-(2-chloroethyl)piperazine (13.9 g) and 4-[3-(1-methylethyl)aminopropyl]phenol (7.0 g) were reacted in the presence of 9.25 ml 4.0N sodium hydroxide in 100 ml dimethylsulfoxide. The crude free base, isolated by extraction using chloroform, was dissolved in ethyl acetate and treated with hydrogen chloride in ethyl acetate to give the crude trihydrochloride salt. Crystallization from methanol-isopropanol yielded 10.8 g of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[3-(1-methylethyl)aminopropyl]phenoxy]ethyl]piperazine trihydrochloride, mp 215°-225°.

Aufarbeitung

  1. customThe crude free base, isolated by extraction
  2. customto give the crude trihydrochloride salt
  3. customCrystallization from methanol-isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-f1b294b188c043268fa78bad8a754356
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04471116

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