Sodium Hydroxide → HCID 13338465, compound

HRID 2418009Notes

Reaction equation

HRID 2418009 reaction equation
[ClH:1].[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Cl:15][C:16]1[CH:29]=[CH:28][C:27]2[S:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][N:36]([CH2:39][CH2:40]Cl)[CH2:35][CH2:34]3)[C:18]=2[CH:17]=1.[OH-].[Na+]>CS(C)=O.O>[ClH:15].[ClH:1].[ClH:15].[Cl:15][C:16]1[CH:29]=[CH:28][C:27]2[S:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][N:36]([CH2:39][CH2:40][O:14][C:11]4[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][CH2:4][NH:3][CH3:2])=[CH:13][CH:12]=4)[CH2:37][CH2:38]3)[C:18]=2[CH:17]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 52754552-Chloro-10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]phenothiazineHCID 13338491HCID 13338491, compound

Product 1

HCID 13338465HCID 13338465, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A solution of 4-(3-methylaminopropoxy)phenol hydrochloride (4.7 g) and 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-(2-chloroethyl)piperazine (10.7 g) (as its dihydrochloride) in dimethylsulfoxide (125 ml) was stirred under nitrogen during the addition of sodium hydroxide (3.46 g) in water (5 ml). The reaction was then stirred at 55° for 4 hours and then was diluted with water (500 ml). The oil which separated was extracted into ethyl acetate and hydrogen chloride was bubbled into the solution previously dried over potassium carbonate to precipitate the crude product as its trihydrochloride salt (4.3 g). Crystallization of the salt from acetonitrile-methanol yielded 1.9 g of 3-[[4-[2-[4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-1-piperazinyl]ethoxy]phenyl]oxy]-N-methylpropanamine trihydrochloride, mp 223°-226°.

Workup

  1. customThe oil which separated
  2. extractionwas extracted into ethyl acetate and hydrogen chloride
  3. customwas bubbled into the solution
  4. dry with materialpreviously dried over potassium carbonate
  5. customto precipitate the crude product as its trihydrochloride salt (4.3 g)
  6. customCrystallization of the salt from acetonitrile-methanol

Sources & evidence

ORD record
ord-de0ada4a5d3041c2941d03132391445b
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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