Triethylamine → Flupimazine

HRID 329044

반응식

HRID 329044 반응식
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:17][CH2:18][CH2:19]Cl)[C:5]=2[CH:4]=1.C(N(CC)CC)C.[NH:30]1[CH2:35][CH2:34][CH:33]([O:36][CH2:37][CH2:38][OH:39])[CH2:32][CH2:31]1>C(C(C)=O)C.[I-].[Na+]>[F:1][C:2]([F:22])([F:21])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:17][CH2:18][CH2:19][N:30]3[CH2:35][CH2:34][CH:33]([O:36][CH2:37][CH2:38][OH:39])[CH2:32][CH2:31]3)[C:5]=2[CH:4]=1

참가 물질

6

반응물 3

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

생성물 1

HCID 218089Flupimazine

시약·촉매·용매 2

HCID 5238Sodium Iodide용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

40 g of 2-trifluoromethyl-10-(3-chloropropyl)-phenothiazine were dissolved in 350 ml of methyl ethyl ketone and 17.6 g of sodium iodide, 11.8 g of triethylamine, then 17 g of 2-(4-piperidyloxy)-ethanol were successively added to this solution. It was refluxed for 20 hours and after cooling, the precipitate was removed by vacuum filtration. The filtrate was evaporated to dryness to obtain 2-trifluoromethyl-10-[3-(4-β-hydroxyethoxypiperidino)-propyl]-phenothiazine as an oil which was added to a mixture of ether and dilute hydrochloric acid. The formed precipitate was recovered by vacuum filtration and was crystallized from 95% ethanol to obtain 40.5 g of 2-trifluoromethyl-10-[-3(4-β-hydroxyethoxypiperidino)-propyl]-phenothiazine hydrochloride as white crystals. Then a current of ammonia was led into an ether suspension of this product and the formed precipitate was removed by filtration. The filtrate was evaporated to dryness to obtain 2-trifluoromethyl-10-[3-(4-β-hydroxyethoxypiperidino)-propyl]-phenothiazine as an oil.

후처리

  1. temperatureIt was refluxed for 20 hours
  2. temperatureafter cooling
  3. customthe precipitate was removed by vacuum filtration
  4. customThe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-44caedd389744c3aa62118cfbc87512f
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04018922

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