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

HRID 2418005Notes

Reaction equation

HRID 2418005 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][O:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=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:43][C:40]4[CH:41]=[CH:42][C:37]([O:36][CH2:35][CH2:34][CH2:33][CH2:32][NH:31][CH:29]([CH3:28])[CH3:30])=[CH:38][CH:39]=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 13338487HCID 13338487, compound

Product 1

HCID 133384531-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[4-(1-methylethyl)aminobutoxy]phenoxy]ethyl]piperazine trihydrochlorideYield 123.7%

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 (3.8 g) and 4-[4-(1-methylethyl)aminobutoxy]phenol (2.0 g), in 100 ml dimethylsulfoxide was reacted with sodium hydroxide (0.4 g) in 3 ml water under the conditions described in method A. The crude amine, extracted into ethyl acetate, was converted to the trihydrochloride salt by addition of excess hydrogen chloride in ethyl acetate to the dried extract. The crude salt was triturated with a small amount of hot methanol, then was crystallized from methanol-ethyl acetate to give 2.0 g of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[4-(1-methylethyl)aminobutoxy]phenoxy]ethyl]piperazine trihydrochloride, mp 220°-221°.

Workup

  1. extractionThe crude amine, extracted into ethyl acetate
  2. additionwas converted to the trihydrochloride salt by addition of excess hydrogen chloride in ethyl acetate to the dried
  3. extractionextract
  4. customThe crude salt was triturated with a small amount of hot methanol
  5. customwas crystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-5164fa11146f41cb849823e190cca9a9
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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