Triethylamine → 2-Trifluoromethyl-10-[3-(4-beta-hydroxyethoxy-4-propylpiperidino)-propyl]-phenothiazine

HRID 329048

反応式

HRID 329048 の反応式
[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.[CH2:30]([C:33]1([O:39][CH2:40][CH2:41][OH:42])[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[CH2:31][CH3:32]>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:36]3[CH2:37][CH2:38][C:33]([O:39][CH2:40][CH2:41][OH:42])([CH2:30][CH2:31][CH3:32])[CH2:34][CH2:35]3)[C:5]=2[CH:4]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 7429410-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazineHCID 214408792-(4-Propyl-4-piperidyloxy)-ethanol

生成物 1

HCID 542643272-Trifluoromethyl-10-[3-(4-beta-hydroxyethoxy-4-propylpiperidino)-propyl]-phenothiazine収率 99.6%

試薬・触媒・溶媒 2

HCID 5238Sodium Iodide溶媒HCID 6569Methyl Ethyl Ketone溶媒2 回

実験手順

10 g of 2-trifluoromethyl-10-(3-chloropropyl)-phenothiazine were dissolved in 50 ml of methyl ethyl ketone and 4.36 g of sodium iodide, 2.9 g of triethylamine, then dropwise a solution of 5.4 g of 2-(4-propyl-4-piperidyloxy)-ethanol in 50 ml of methyl ethyl ketone were added successively thereto. The mixture was refluxed for 24 hours and after cooling, the precipitate formed was removed by vacuum filtration. The precipitate formed was removed by filtration and the filtrate was evaporated in vacuo and the residue was dissolved in methylene chloride. The organic solution was washed with an aqueous solution of sodium bicarbonate, then with water and the solution was dried and concentrated in vacuo to obtain 14.2 g of 2-trifluoromethyl-10-[3-(4-β-hydroxyethoxy-4-propylpiperidino)-propyl]-phenothiazine as a beige product which was dissolved in 50 ml of ethanol. The resulting solution was reacted with an ether solution of hydrogen chloride and the hydrochloride was precipitated by the addition of ether. The said precipitate was recovered by vacuum filtration and was washed with ether and crystallized from acetonitrile to obtain 7 g of 2-trifluoromethyl-10-[3-(4-β-hydroxyethoxy-4-propylpiperidino)-propyl]-phenothiazine hydrochloride as white crystals melting at 192° C.

後処理

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperatureafter cooling
  3. customthe precipitate formed
  4. customwas removed by vacuum filtration
  5. customThe precipitate formed
  6. customwas removed by filtration
  7. customthe filtrate was evaporated in vacuo
  8. dissolutionthe residue was dissolved in methylene chloride
  9. washThe organic solution was washed with an aqueous solution of sodium bicarbonate
  10. dry with materialwith water and the solution was dried
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cb32354199474c3facec98c1d8c1246b
出典データセット
uspto-grants-1977_04
特許番号
US04018922

関連ノート

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