Hydrochloric Acid → HCID 14349082, compound

HRID 704682Notes

Reaction equation

HRID 704682 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 any oil. This oil was converted to the maleate salt (8 g, 74%, m.p. 95°-100° C.) by the addition of ethereal 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 any oil
  8. additionThis oil was converted to the maleate salt (8 g, 74%, m.p. 95°-100° C.) by the addition of ethereal maleic acid of which 4 g
  9. customwas recrystallized twice from isopropanol-ether

Sources & evidence

ORD record
ord-51f52b23d3694df4a3d9e42d14ad6ec9
Source dataset
uspto-grants-1991_01
Patent number
US04988690

Reaction notes

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