Propionyl chloride → HCID 70514181, compound

HRID 1632681Notes

Reaction equation

HRID 1632681 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(=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

Participants

5

Reactant 3

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

Product 1

HCID 70514181HCID 70514181, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-deec0eabc4764fc8b46814cbfbc5a9de
Source dataset
uspto-grants-1984_10
Patent number
US04477378

Reaction notes

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