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

HRID 2418004Notes

Reaction equation

HRID 2418004 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

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°.

Workup

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

Sources & evidence

ORD record
ord-f1b294b188c043268fa78bad8a754356
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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