2-Chloro-10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]phenothiazine → (R)-1-(1-methylethylamino)-3-[4-[2-[4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl]ethoxy]phenoxy]-2-propanol, trihydrochloride
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.[OH:28][C:29]1[CH:43]=[CH:42][C:32]([O:33][CH2:34][C@H:35]([OH:41])[CH2:36][NH:37][CH:38]([CH3:40])[CH3:39])=[CH:31][CH:30]=1>>[ClH:1].[ClH:1].[ClH:1].[CH3:40][CH:38]([NH:37][CH2:36][C@@H:35]([OH:41])[CH2:34][O:33][C:32]1[CH:31]=[CH:30][C:29]([O:28][CH2:26][CH2:25][N:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][N:5]3[C:4]4[CH:3]=[C:2]([Cl:1])[CH:15]=[CH:14][C:13]=4[S:12][C:11]4[C:6]3=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH2:24][CH2:23]2)=[CH:43][CH:42]=1)[CH3:39]Participants
3
Reactant 2
Product 1
Procedure
Using the conditions outlined in method A, 11.7 g of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-(2-chloroethyl)piperazine was reacted with 7.5 g of (R)-1-(4-hydroxyphenoxy)-3-(1-methylethyl)amino-2-propanol to give, after recrystallization from methanol-ethyl acetate and from methanol-ethanol, the trihydrochloride salt of (S)-1-(1-methylethylamino)-3-[4-[2-[4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl]ethoxy]phenoxy]-2-propanol, trihydrochloride, mp 251.5°-253°; [α]D25 +10.37° (c, 1.0, methanol).
Workup
- customto give
- customafter recrystallization from methanol-ethyl acetate
Sources & evidence
- ORD record
- ord-72bd0bb9b8204434ac949e096d2a792a
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04471116
Reaction notes
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