Chloride → (S)-1-(1-methylethylamino)-3-[4-[2-[4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl]ethoxy]phenoxy]-2-propanol

HRID 2418000Notes

Reaction equation

HRID 2418000 reaction equation
[Cl-].[Cl:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27]Cl)[CH2:22][CH2:21]3)[C:5]=2[CH:4]=1.[OH:29][C:30]1[CH:44]=[CH:43][C:33]([O:34][CH2:35][C@@H:36]([OH:42])[CH2:37][NH:38][CH:39]([CH3:41])[CH3:40])=[CH:32][CH:31]=1>CS(C)=O.O.[OH-].[Na+]>[CH3:41][CH:39]([NH:38][CH2:37][C@H:36]([OH:42])[CH2:35][O:34][C:33]1[CH:32]=[CH:31][C:30]([O:29][CH2:27][CH2:26][N:23]2[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][N:6]3[C:5]4[CH:4]=[C:3]([Cl:2])[CH:16]=[CH:15][C:14]=4[S:13][C:12]4[C:7]3=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH2:25][CH2:24]2)=[CH:44][CH:43]=1)[CH3:40]

Participants

7

Reactant 3

HCID 312ChlorideHCID 42396PrenalterolHCID 52754552-Chloro-10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]phenothiazine

Product 1

HCID 13338445(S)-1-(1-methylethylamino)-3-[4-[2-[4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl]ethoxy]phenoxy]-2-propanolYield 94.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of the chloride of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-(2-chloroethyl)piperazine (9.4 g) in 75 ml dimethylsulfoxide was added (S)-1-(4-hydroxyphenoxy)-3-(1-methylethyl)amino-2-propanol (6.0 g) followed by 6.25 ml 4N sodium hydroxide solution. The mixture was stirred under argon at 55° for 2 hours then was cooled and diluted with 500 ml water and 35 ml 1N sodium hydroxide, and extracted with dichloromethane (3×). The extracts were backwashed with water (2×), dried over potassium carbonate and the solvent was removed in vacuo to give 12.8 g of crude (S)-1-(1-methylethylamino)-3-[4-[2-[4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl]ethoxy]phenoxy]-2-propanol as an oil.

Workup

  1. temperaturethen was cooled
  2. extractionextracted with dichloromethane (3×)
  3. dry with materialdried over potassium carbonate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-06c7fe9c5ef3451992f8c37ab05826b5
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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