Sodium Hydroxide → HCID 13338455, compound

HRID 2418006Notes

Reaction equation

HRID 2418006 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][CH2:35][CH2:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=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[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][O:44][C:41]4[CH:42]=[CH:43][C:38]([O:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][NH:31][CH:29]([CH3:28])[CH3:30])=[CH:39][CH:40]=4)[CH2:23][CH2:24]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 133384884-[5-(1-Methylethyl)aminopentoxy]phenol

Product 1

HCID 13338455HCID 13338455, compoundYield 145.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-(2-chloroethyl)piperazine (9.2 g) and 4-[5-(1-methylethyl)aminopentoxy]phenol (5.16 g) in 150 ml dimethylsulfoxide was treated with sodium hydroxide (0.87 g) in water (7 ml) and was stirred at 55°-60° for 5 hours. The usual work-up furnished the crude trihydrochloride salt which was recrystallized from methanol to give 5.8 g of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[5-(1-methylethyl)aminopentoxy]phenoxy]ethyl]piperazine trihydrochloride, mp 237°-239°.

Workup

  1. customThe usual work-up furnished the crude trihydrochloride salt which
  2. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-3b8eed28d3314fcebd3f66052729777b
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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