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Dichloromethane → (cis)-3-(Hydroxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluormethyl)-2H-1-benzazepin-2-one, monohydrochloride

HRID 1253308
ノート
印刷プレビュー

反応式

HRID 1253308 の反応式
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[CH:10]([OH:14])[CH:9]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:8][C:7]=2[CH:23]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].Br.[CH3:38][N:39]([CH3:43])[CH2:40][CH2:41]Br.[Cl:44]CCl>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[ClH:44].[OH:14][C@H:10]1[C@@H:9]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:8][C:7]2[CH:23]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:4]=[CH:5][C:6]=2[N:12]([CH2:41][CH2:40][N:39]([CH3:43])[CH3:38])[C:11]1=[O:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 141562187-(trifluoromethyl)-1,3,4,5-tetrahydro-3-hydroxy-4-(4-methoxyphenyl)-2H-1-benzazepin-2-oneHCID 17749109Barium hydroxide, octahydrateHCID 457913472-Bromoethyldimethylammonium bromide2 回

生成物 1

HCID 131715557(cis)-3-(Hydroxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluormethyl)-2H-1-benzazepin-2-one, monohydrochloride

試薬・触媒・溶媒 2

HCID 5963Benzyltrimethylammonium chloride触媒HCID 962Water溶媒2 回

実験手順

A suspension of 7-(trifluoromethyl)-1,3,4,5-tetrahydro-3-hydroxy-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (1.0 g, 2.85 mmol; see Example 28E) in 20 ml of dichloromethane was treated with 3.6 ml of water followed by the addition of barium hydroxide octahydrate (1.89 g, 5.99 mmol) and benzyl trimethylammonium chloride (0.12 g, 0.63 mmol). A solution of 2-dimethylaminoethyl bromide, hydrobromide in 2 ml of water was added portionwise with a pipette. Vigorous stirring under argon was carried out for 72 hours. An additional 0.33 g of 2-dimethylaminoethyl bromide, hydrobromide was added and stirring was continued overnight. The reaction mixture was filtered. The dichloromethane layer was washed twice with water. Hydrochloric acid (1M) was added, the dichloromethane was removed in vacuo, the aqueous layer was washed three times with ethyl acetate, made basic with 1M sodium hydroxide solution, and washed three times with ethyl acetate. The ethyl acetate layers were dried over sodium sulfate and evaporated in vacuo to yield 0.52 g of a white solid. Evaporation in vacuo of the ethyl acetate layers from the 1M hydrochloric acid washes yielded 0.52 g of a tan solid which was dissolved in chloroform, treated with saturated hydrogen chloride-ether solution and triturated with ether.

後処理

  1. stirringstirring
  2. waitwas continued overnight
  3. filtrationThe reaction mixture was filtered
  4. washThe dichloromethane layer was washed twice with water
  5. additionHydrochloric acid (1M) was added
  6. customthe dichloromethane was removed in vacuo
  7. washthe aqueous layer was washed three times with ethyl acetate
  8. washwashed three times with ethyl acetate
  9. dry with materialThe ethyl acetate layers were dried over sodium sulfate
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a82bcd00548345668957046a33908ce9
出典データセット
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04748239

反応ノート

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