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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
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HRID 1253308 반응식
[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]
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참가 물질

7

반응물 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 bromide2회

생성물 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

시약·촉매·용매 2

HCID 5963Benzyltrimethylammonium chloride촉매HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a82bcd00548345668957046a33908ce9
출처 데이터셋
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04748239

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