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Ethyl Acetate → Deacetyldiltiazem hydrochloride

HRID 1903702
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HRID 1903702 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][Cl:27].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[ClH:27].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:7][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-HCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

생성물 1

HCID 12449428Deacetyldiltiazem hydrochloride수율 92.8%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

A mixture of 30.1 g of cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one, 18.7 g of 2-(dimethylamino)ethyl chloride hydrochloride, 33.0 g of potassium carbonate and 240 ml of ethyl acetate is refluxed for 30 minutes under stirring. Then, 5 ml of water are added to the mixture, and the aqueous mixture is further refluxed for 6 hours under stirring. After cooling the reaction mixture, said mixture is washed with water. The ethyl acetate layer is separated and washed with water. The ethyl acetate layer is then evaporated under reduced pressure to remove ethyl acetate. The residue is dissolved in ethanol. After cooling the solution, said solution is acidified with 10% HCl/ethanol and then stirred at a temperature below 10° C. for 5 hours. The crystalline precipitates are collected by filtration, washed with ethanol and then dried. 37.9 g of cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepine-4(5H)-one hydrochloride are thereby obtained. Yield: 92.7%

후처리

  1. temperatureis refluxed for 30 minutes
  2. temperaturethe aqueous mixture is further refluxed for 6 hours
  3. stirringunder stirring
  4. temperatureAfter cooling the reaction mixture
  5. washis washed with water
  6. customThe ethyl acetate layer is separated
  7. washwashed with water
  8. customThe ethyl acetate layer is then evaporated under reduced pressure
  9. customto remove ethyl acetate
  10. dissolutionThe residue is dissolved in ethanol
  11. temperatureAfter cooling the solution
  12. stirringstirred at a temperature below 10° C. for 5 hours
  13. customThe crystalline precipitates
  14. filtrationare collected by filtration
  15. washwashed with ethanol
  16. customdried

출처 및 근거

ORD 기록
ord-c7166a5db9a448348de3500484cd35c2
출처 데이터셋
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04438035

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