Benzoyl chloride → HCID 70514137, compound

HRID 1632682Notes

Reaction equation

HRID 1632682 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 70514137HCID 70514137, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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-1H-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 1N ethereal hydrogen chloride. Obtain an analytical sample by crystallization from 2-propanol, m.p. 257°-258° C., [α]D26 =+10.0° (c=1, dimethylformamide).

Workup

  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 1N 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)

Sources & evidence

ORD record
ord-c2071077a2fb4322b507e6222123c9ae
Source dataset
uspto-grants-1984_10
Patent number
US04477378

Reaction notes

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