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

HRID 329037

반응식

HRID 329037 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-889f9245fe624fdbbb11d67bcb861e23
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04018922

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