Hydrochloric Acid → HCID 21312831, compound

HRID 971607

Reaction equation

HRID 971607 reaction equation
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]([OH:19])[C:3]=1[OH:20].[CH2:21]1[O:23][CH2:22]1.Cl>CC(C)=O.C(OCC)(=O)C.C(O)C>[ClH:1].[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([CH2:21][CH2:22][OH:23])[CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]([OH:19])[C:3]=1[OH:20]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 1218SK&F 81297HCID 6354Ethylene Oxide

Product 1

HCID 21312831HCID 21312831, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 3.9 g sample of 6-chloro-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-chloro-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-9bdc1a1dcd2d48fbad589ea006bd6747
Source dataset
uspto-grants-1979_07
Patent number
US04160765

Linked notes

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