Sodium Iodide → Ethanol, 2-((1-(3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propyl)-4-piperidinyl)oxy)-, hydrochloride (1:1)

HRID 329037

Reaction equation

HRID 329037 reaction equation
[I-].[Na+].[Cl:3][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.[NH:32]1[CH2:37][CH2:36][CH:35]([O:38][CH2:39][CH2:40][OH:41])[CH2:34][CH2:33]1>C(C(C)=O)C>[ClH:3].[OH:41][CH2:40][CH2:39][O:38][CH:35]1[CH2:36][CH2:37][N:32]([CH2:4][CH2:5][CH2:6][N:7]2[C:20]3[CH:19]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:16][C:15]=3[S:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:33][CH2:34]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 7429410-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazineHCID 202953322-(Piperidin-4-yloxy)ethan-1-ol

Product 1

HCID 218088Ethanol, 2-((1-(3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propyl)-4-piperidinyl)oxy)-, hydrochloride (1:1)Yield 71%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

17.6 g (0.117 mole) of sodium iodide were added to a solution of 40 g (0.17 mole) of 10-(3-chloropropyl)-2-trifluoromethyl-phenothiazine in 350 ml of methyl ethyl ketone followed by the addition of first 11.8 g (0.117 mole) of triethylamine and then 17 g (0.117 mole) of 2-(4-piperidyloxy)-ethanol. The resulting solution was refluxed for 20 hours and after cooling, the precipitate was removed by vacuum filtration. The filtrate was evaporated to dryness. The oil residue was stirred with a mixture of ether and dilute hydrochloric acid and the precipitate formed was recovered by vacuum filtration and crystallized from a 95% ethanol-ether mixture to obtain 40.5 g (71% yield) of 10-[3-(4-β-hydroxyethoxypiperidino) propyl]-2-trifluoromethyl-phenothiazine hydrochloride in the form of white crystals melting at 218°-219° C on a heated microscopic stage.

Workup

  1. temperatureThe resulting solution was refluxed for 20 hours
  2. temperatureafter cooling
  3. customthe precipitate was removed by vacuum filtration
  4. customThe filtrate was evaporated to dryness
  5. customthe precipitate formed
  6. filtrationwas recovered by vacuum filtration
  7. customcrystallized from a 95% ethanol-ether mixture

Sources & evidence

ORD record
ord-889f9245fe624fdbbb11d67bcb861e23
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Linked notes

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