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

HRID 2418001Notes

Reaction equation

HRID 2418001 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[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:42][C:43]1[CH:57]=[CH:56][C:46]([O:47][CH2:48][C@@H:49]([OH:55])[CH2:50][NH:51][CH:52]([CH3:54])[CH3:53])=[CH:45][CH:44]=1.[OH-].[Na+]>CS(C)=O>[CH3:54][CH:52]([NH:51][CH2:50][C@H:49]([OH:55])[CH2:48][O:47][C:46]1[CH:45]=[CH:44][C:43]([O:42][CH2:40][CH2:39][N:36]2[CH2:35][CH2:34][N:33]([CH2:32][CH2:31][CH2:30][N:19]3[C:18]4[CH:17]=[C:16]([Cl:15])[CH:29]=[CH:28][C:27]=4[S:26][C:25]4[C:20]3=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:38][CH2:37]2)=[CH:57][CH:56]=1)[CH3:53]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 42396PrenalterolHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 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 87.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of the dihydrochloride salt of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-(2-chloroethyl)piperazine (12.4 g) and (S)-1-(4-hydroxyphenoxy)-3-(1-methylethyl)amino-2-propanol (6.2 g) in 100 ml dimethylsulfoxide was added 15.25 ml of 5N sodium hydroxide solution and the mixture was stirred under argon for 2 hours at 50°. The reaction was worked up as in method A to give 14.7 g of the crude (S)-1-(1-methylethylamino)-3-[4-[2-[4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl]ethoxy]phenoxy]-2-propanol.

Sources & evidence

ORD record
ord-7abf18dd720545189a4c00898dc0d5c4
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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