Hydrochloric Acid → HCID 20394972, compound

HRID 261448Notes

Reaction equation

HRID 261448 reaction equation
[C:1]([C:5]1[C:15]2[CH2:14][CH2:13][NH:12][CH2:11][CH:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH:8]=[C:7]([OH:22])[C:6]=1[OH:23])([O:3][CH3:4])=[O:2].[CH2:24]1[O:26][CH2:25]1.[ClH:27]>CC(C)=O.C(OCC)(=O)C.C(O)C>[ClH:27].[C:1]([C:5]1[C:15]2[CH2:14][CH2:13][N:12]([CH2:24][CH2:25][OH:26])[CH2:11][CH:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:9]=2[CH:8]=[C:7]([OH:22])[C:6]=1[OH:23])([O:3][CH3:4])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 203949406-carbomethoxy-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 20394972HCID 20394972, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 4.2 g sample of 6-carbomethoxy-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine is slurried in 25 ml of acetone and 0.7 g (0.016 mol, 10% excess) of ethylene oxide is added. The mixture is placed in a pressure bottle and stirred at ambient temperature for about 40 hours. The reaction mixture is then heated to 60°-80° for 30 minutes, cooled and filtered. Concentration of the filtrate gives a solid which is taken up in ethyl acetate and reprecipitated with ether. The solid thus obtained is dissolved in ethanol and treated with ethereal hydrogen chloride to give 6-carbomethoxy-7,8-dihydroxy-3-(2-hydroxyethyl)-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride.

Workup

  1. temperatureThe reaction mixture is then heated to 60°-80° for 30 minutes
  2. temperaturecooled
  3. filtrationfiltered
  4. customConcentration of the filtrate gives a solid which
  5. customreprecipitated with ether
  6. customThe solid thus obtained

Sources & evidence

ORD record
ord-f87c2c27525349a7b362ce8a46a16a99
Source dataset
uspto-grants-1979_08
Patent number
US04165372

Reaction notes

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