Reaction equation
[I-].[Na+].Cl[CH2:4][CH2:5][CH2:6][N:7]1[C:20]2[CH:19]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.C(N(CC)CC)C.[CH3:32][CH:33]([OH:43])[CH:34]([CH3:42])[O:35][CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>C(C(C)=O)C>[F:22][C:21]([F:24])([F:23])[C:18]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:6][CH2:5][CH2:4][N:39]3[CH2:40][CH2:41][CH:36]([O:35][CH:34]([CH3:42])[CH:33]([CH3:32])[OH:43])[CH2:37][CH2:38]3)[C:20]=2[CH:19]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
22.5 g (0.15 mole) of sodium iodide were added to a solution of 51.5 g (0.15 mole) of 10-(3-chloropropyl)-2-trifluoromethyl-phenothiazine in 400 ml of methyl ethyl ketone followed by the addition of 15.2 g (0.15 mole) of triethylamine and then 26 g (0.15 mole) of 1,2-dimethyl-2-(4-piperidyloxy)-ethanol. The mixture was then refluxed for 20 hours and after cooling, the precipitate formed was removed by vacuum filtration. The filtrate was evaporated to dryness and the oil residue was chromatographed over 1 kg of neutral alumina. Elution with ethyl acetate gave 34.5 g (48% yield) of 2-trifluoromethyl-10-[3-(4-[1,2-dimethyl-2-hydroxyethoxy]-piperidino)-propyl]-phenothiazine in the form of a clear amber oil.
Workup
- temperatureThe mixture was then refluxed for 20 hours
- temperatureafter cooling
- customthe precipitate formed
- customwas removed by vacuum filtration
- customThe filtrate was evaporated to dryness
- customthe oil residue was chromatographed over 1 kg of neutral alumina
- washElution with ethyl acetate
Sources & evidence
- ORD record
- ord-e8008bdff8df4e0796e205ef0c9844a3
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04018922
Linked notes
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