Hydrochloric Acid → HCID 20316639, compound

HRID 2419020Notes

Reaction equation

HRID 2419020 reaction equation
[OH:1][C:2]1[C:20]([OH:21])=[CH:19][C:5]2[CH:6]([C:11]3[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=3)[CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH2:22]1[O:24][CH2:23]1.[ClH:25]>CC(C)=O.C(OCC)(=O)C.C(O)C>[ClH:25].[OH:1][C:2]1[C:20]([OH:21])=[CH:19][C:5]2[CH:6]([C:11]3[CH:12]=[CH:13][C:14]([S:17][CH3:18])=[CH:15][CH:16]=3)[CH2:7][N:8]([CH2:22][CH2:23][OH:24])[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 20316651HCID 20316651, compound

Product 1

HCID 20316639HCID 20316639, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 4 g sample of 7,8-dihydroxy-1-(p-methylthiophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine is slurred in 25 ml of acetone and 0.8 g ( ~ 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 7,8-dihydroxy-3-(2-hydroxyethyl)-1-(p-methylthiophenyl)-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-51a930f781ba4755b9f4eb7c839a6a71
Source dataset
uspto-grants-1978_08
Patent number
US04104379

Reaction notes

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