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

HRID 2418003Notes

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

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 679Dimethyl SulfoxideSolventHCID 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
Patent number
US04471116

Reaction notes

Loading…