Triethylamine → 2-Trifluoromethyl-10-[3-(4-heptyl-4-beta-hydroxy-ethoxy-piperidino)-beta-propyl]-phenothiazine hydrochloride

HRID 329049

반응식

HRID 329049 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]C[Cl:20])[C:5]=2[CH:4]=1.[CH2:23](N(CC)CC)C.[CH2:30]([C:37]1([O:43][CH2:44][CH2:45][OH:46])[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(C(C)=O)C.[I-].[Na+]>[ClH:20].[F:21][C:2]([F:22])([F:1])[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]([CH:17]([CH2:23][N:40]3[CH2:41][CH2:42][C:37]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([O:43][CH2:44][CH2:45][OH:46])[CH2:38][CH2:39]3)[CH3:18])[C:5]=2[CH:4]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 7429410-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazineHCID 214409012-(4-Heptyl-4-piperidyloxy)-ethanol

생성물 1

HCID 706346132-Trifluoromethyl-10-[3-(4-heptyl-4-beta-hydroxy-ethoxy-piperidino)-beta-propyl]-phenothiazine hydrochloride수율 32.4%

시약·촉매·용매 2

HCID 5238Sodium Iodide용매HCID 6569Methyl Ethyl Ketone용매2회

실험 절차

14.1 g of 2-trifluoromethyl-10-(3-chloropropyl)-phenothiazine were dissolved in 50 ml of methyl ethyl ketone and 6.14 g of sodium iodide, 4.15 g of triethylamine, then 10 g of 2-(4-heptyl-4-piperidyloxy)-ethanol dissolved in 50 ml of methyl ethyl ketone were successively added thereto. The mixture was refluxed with agitation for 40 hours and after cooling, the precipitate formed was removed by vacuum filtration. The organic solution was washed with an aqueous solution of sodium bicarbonate, then with water, dried and then concentrated. The said product was reacted with an ether solution of hydrogen chloride and the obtained precipitate was recovered by vacuum filtration and was crystallized from an ethanol ether mixture to obtain 7.8 g of 2-trifluoromethyl-10-[3-(4-heptyl-4-β-hydroxy-ethoxy-piperidino)-β-propyl]-phenothiazine hydrochloride as white crystals melting at 180° C and soluble in ethanol and insoluble in water and ether.

후처리

  1. additionwere successively added
  2. temperatureThe mixture was refluxed with agitation for 40 hours
  3. temperatureafter cooling
  4. customthe precipitate formed
  5. customwas removed by vacuum filtration
  6. washThe organic solution was washed with an aqueous solution of sodium bicarbonate
  7. dry with materialwith water, dried
  8. concentrationconcentrated
  9. customThe said product was reacted with an ether solution of hydrogen chloride
  10. filtrationthe obtained precipitate was recovered by vacuum filtration
  11. customwas crystallized from an ethanol ether mixture

출처 및 근거

ORD 기록
ord-2ac11dbfba764ba3a22b4f086f28994b
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04018922

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