Propionyl chloride → HCID 70514181, 화합물

HRID 1632681노트

반응식

HRID 1632681 반응식
[Cl:1][C:2]1[C:19]([OH:20])=[CH:18][C:5]2[C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][N:8]([CH3:11])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C(=O)(O)[O-].[Na+].[C:26](Cl)(=[O:29])[CH2:27][CH3:28]>C(#N)C>[ClH:1].[Cl:1][C:2]1[C:19]([O:20][C:26](=[O:29])[CH2:27][CH3:28])=[CH:18][C:5]2[C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][N:8]([CH3:11])[CH2:9][CH2:10][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 6603800(5S)-8-Chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

생성물 1

HCID 70514181HCID 70514181, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Reflux a mixture of 6.70 g (0.0232) moles of (S)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine, 8.0 g of anhydrous sodium bicarbonate and 6.0 ml of propionyl chloride in 150 ml of dry acetonitrile with stirring for 2.5 hours and concentrate to dryness on a steam bath. Dissolve the residue in a mixture of 60 ml of water and 70 ml of ethyl ether. Separate the ether layer, dry over anhydrous sodium sulfate, filter and evaporate to dryness. Redissolve the residue in 150 ml of anhydrous ethyl ether and precipitate (S)-7-chloro-3-methyl-1-phenyl-8-propionyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride by slow addition of a slight excess of 1N ethereal hydrogen chloride. Obtain an analytical sample by crystallization from 2-propanol, m.p. 234°-236° C., [α]D26 =+32.5° (c=1, dimethylformamide).

후처리

  1. temperatureReflux
  2. concentrationconcentrate to dryness on a steam bath
  3. dissolutionDissolve the residue
  4. additionin a mixture of 60 ml of water and 70 ml of ethyl ether
  5. customSeparate the ether layer
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationfilter
  8. customevaporate to dryness
  9. dissolutionRedissolve the residue in 150 ml of anhydrous ethyl ether
  10. customprecipitate (S)-7-chloro-3-methyl-1-phenyl-8-propionyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
  11. additionby slow addition of a slight excess of 1N ethereal hydrogen chloride
  12. customObtain an analytical sample
  13. customby crystallization from 2-propanol, m.p. 234°-236° C., [α]D26 =+32.5° (c=1, dimethylformamide)

출처 및 근거

ORD 기록
ord-deec0eabc4764fc8b46814cbfbc5a9de
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04477378

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