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Sodium Hydroxide → 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[2-(1-methylethyl)aminoethoxy]phenoxy]ethyl]piperazine trihydrochloride

HRID 2418003
Notes
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Reaction equation

HRID 2418003 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][O:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1)[CH3:30].[OH-].[Na+]>CS(C)=O.O>[ClH:1].[ClH:1].[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[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][O:41][C:38]4[CH:37]=[CH:36][C:35]([O:34][CH2:33][CH2:32][NH:31][CH:29]([CH3:30])[CH3:28])=[CH:40][CH:39]=4)[CH2:21][CH2:20]3)[C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 52754552-Chloro-10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]phenothiazineHCID 133384854-[2-(1-Methylethyl)aminoethoxy]phenol

Product 1

HCID 133384491-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[2-(1-methylethyl)aminoethoxy]phenoxy]ethyl]piperazine trihydrochloride

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Procedure

Using the conditions essentially described in method A above, 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-(2-chloroethyl)piperazine (10.6 g) was reacted with 4-[2-(1-methylethyl)aminoethoxy]phenol (4.88) in dimethylsulfoxide (125 ml) containing sodium hydroxide (1.0 g) in water (7 ml). The crude free base was extracted using ethyl acetate and the dried extract was treated with excess hydrogen chloride in ethyl acetate to furnish the crude trihydrochloride salt. Crystallization of the crude from methanol-isopropanol afforded 2.5 g of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[2-(1-methylethyl)aminoethoxy]phenoxy]ethyl]piperazine trihydrochloride, mp 223°-235°.

Workup

  1. extractionThe crude free base was extracted
  2. extractionthe dried extract
  3. additionwas treated with excess hydrogen chloride in ethyl acetate
  4. customto furnish the crude trihydrochloride salt
  5. customCrystallization of the crude from methanol-isopropanol

Sources & evidence

ORD record
ord-06a769da662249408938ebbbbd8cf95a
Source dataset
uspto-grants-1984_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04471116

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes