Benzoyl chloride → HCID 70514137、化合物

HRID 1702752ノート

反応式

HRID 1702752 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 70514137HCID 70514137、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-771bd31a1e70474785ad43281c477e1b
出典データセット
uspto-grants-1982_09
特許番号
US04349472

反応ノート

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