Hydrochloric Acid → HCID 14349081, compound

HRID 346070Notes

Reaction equation

HRID 346070 reaction equation
C(O)(=O)C(O)=O.[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)CCC1=O>CO>[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 14349081HCID 14349081, 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 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 meleate, 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 ethereal maleic acid of which 4 g
  9. customwas recrystallized twice from isopropanol-ether

Sources & evidence

ORD record
ord-8651ed7fca454495a2e59f9ac0ecc16c
Source dataset
uspto-grants-1991_10
Patent number
US05059688

Reaction notes

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