Hydrochloric Acid → HCID 14349082, compound

HRID 414822Notes

Reaction equation

HRID 414822 reaction equation
[C:1](O)(=O)[C:2]([OH:4])=[O:3].[CH3:7][O:8][C:9]1[C:26]([O:27][CH3:28])=[CH:25][C:12]2[CH:13]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][NH:15][CH2:16][CH2:17][C:11]=2[CH:10]=1.Cl.[Br:30]N1C(=[O:36])CCC1=O>CO>[C:26]([OH:27])(=[O:36])/[CH:9]=[CH:1]\[C:2]([OH:4])=[O:3].[Br:30][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH:13]2[C:12]3[CH:25]=[C:26]([O:27][CH3:28])[C:9]([O:8][CH3:7])=[CH:10][C:11]=3[CH2:17][CH2:16][NH:15][CH2:14]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 14349062HCID 14349062, compound

Product 1

HCID 14349082HCID 14349082, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7,8-dimethoxy-1-phenoxy-2,3,4,5-tetrahydro-3-benzazepine of Example 35 (6.5 g, 22 mmole) in 300 ml methanol was acidified to pH 1 with ethereal hydrogen chloride. After this solution was cooled with an ice bath, N-bromosuccinimide (4.2 g, 24 mmole) was added. The reaction mixture slowly warmed to ambient temperature, was evaporated, stirred with water, basified with saturated sodium carbonate and was extracted with ethyl acetate-ether. The organic extracts were washed with water, saturated sodium chloride and were dried (anhydrous MgSO4), filtered and evaporated to 8 g of an oil. This oil was converted to the maleate salt (8 g, 74%, m.p. 95°-100° C.) by the addition of etheral maleic acid of which 4 g was recrystallized twice from isopropanol-ether to give 2.4 g (45%) of 1-(4-bromophenoxy)-7,8-dimethoxy-2,3,4,5-tetrahydro-3-benzazepine maleate, d 145°-146° C.

Workup

  1. temperatureAfter this solution was cooled with an ice bath
  2. customwas evaporated
  3. extractionwas extracted with ethyl acetate-ether
  4. washThe organic extracts were washed with water, saturated sodium chloride
  5. dry with materialwere dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. customevaporated to 8 g of an oil
  8. additionThis oil was converted to the maleate salt (8 g, 74%, m.p. 95°-100° C.) by the addition of etheral maleic acid of which 4 g
  9. customwas recrystallized twice from isopropanol-ether

Sources & evidence

ORD record
ord-f9df7ab34bc8447397430e95eda18979
Source dataset
uspto-grants-1988_12
Patent number
US04794181

Reaction notes

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