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Hydrochloric Acid → methyl 7-[4-(2-ethoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586842
Notes
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Reaction equation

HRID 586842 reaction equation
C(OC([N:8]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][CH2:29][CH3:30])=[CH:21][CH:20]=3)=[CH:18][C:13]=2[CH:12]=[C:11]([C:31]([O:33][CH3:34])=[O:32])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.[OH-].[Na+]>C(OCC)(=O)C>[CH2:29]([O:28][CH2:27][CH2:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[CH:16]=[CH:15][C:14]3[NH:8][CH2:9][CH2:10][C:11]([C:31]([O:33][CH3:34])=[O:32])=[CH:12][C:13]=3[CH:18]=2)=[CH:24][CH:23]=1)[CH3:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22328996methyl 1-(t-butoxycarbonyl)-7-[4-(2-ethoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22329032methyl 7-[4-(2-ethoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
80 °C

Procedure

In ethyl acetate (50 ml) was dissolved methyl 1-(t-butoxycarbonyl)-7-[4-(2-ethoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.1 g). To the solution was added 6N hydrochloric acid (20 ml), and the mixture was stirred at 80° C. for 45 minutes, neutralized with 1N sodium hydroxide solution and was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, and the solvent was evaporated to give methyl 7-[4-(2-ethoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.7 g) as yellow crystals.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-89fa452063614de180e1f0ce70001422
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06936602B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes