Benzoyl chloride → HCID 70514137, 화합물

HRID 1702752노트

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HRID 1702752 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:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[ClH:1].[C:21]([O:20][C:19]1[C:2]([Cl:1])=[CH:3][C:4]2[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][C@@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH:18]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 6603800(5S)-8-Chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

생성물 1

HCID 70514137HCID 70514137, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Reflux for 5 hours with stirring a mixture of 1.20 g (0.00417 moles) of (S)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1-H-3-benzazepine (obtained in step E of Example 1), 2.0 ml (0.017 moles) of benzoyl chloride and 2.5 g of anhydrous sodium bicarbonate in 40 ml of dry acetonitrile. Evaporate to dryness on a steam bath under reduced pressure (about 100 mm). Dissolve the residue by stirring for 2 hours at 10° C. in a mixture of 50 ml each of water and ethyl ether. Separate the ether layer, dry over anhydrous sodium sulfate, and evaporate to dryness. Redissolve the residue in 50 ml of anhydrous ethyl ether and precipitate (S)-8-benzoyloxy-7-chloro-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride with 1 N ethereal hydrogen chloride. Obtain an analytical sample by crystallization from 2-propanol, m.p. 257°-258° C., [α]D26 =+10.0° (c=1, dimethylformamide).

후처리

  1. temperatureReflux for 5 hours
  2. customEvaporate to dryness on a steam bath under reduced pressure (about 100 mm)
  3. dissolutionDissolve the residue
  4. stirringby stirring for 2 hours at 10° C. in a mixture of 50 ml each of water and ethyl ether
  5. customSeparate the ether layer
  6. dry with materialdry over anhydrous sodium sulfate
  7. customevaporate to dryness
  8. dissolutionRedissolve the residue in 50 ml of anhydrous ethyl ether
  9. customprecipitate (S)-8-benzoyloxy-7-chloro-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride with 1 N ethereal hydrogen chloride
  10. customObtain an analytical sample
  11. customby crystallization from 2-propanol, m.p. 257°-258° C., [α]D26 =+10.0° (c=1, dimethylformamide)

출처 및 근거

ORD 기록
ord-771bd31a1e70474785ad43281c477e1b
출처 데이터셋
uspto-grants-1982_09
특허 번호
US04349472

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