Hydrochloric Acid → 5-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

HRID 54752

Reaction equation

HRID 54752 reaction equation
[BH4-].[Li+].C([O:5][C:6]([CH2:8][O:9][CH:10]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[N:14]([C:22](=[O:39])[C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:37])=[CH:25][CH:24]=2)[CH2:13][CH2:12][CH2:11]1)=O)C.Cl>O1CCCC1>[OH:5][CH2:6][CH2:8][O:9][CH:10]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[N:14]([C:22](=[O:39])[C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:37])=[CH:25][CH:24]=2)[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 189173325-ethoxycarbonylmethoxy-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 189174515-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepineYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.28 g of lithium borohydride was added to a solution of 2.2 g of 5-ethoxycarbonylmethoxy-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine dissolved in 50 ml of tetrahydrofuran, at room temperature with stirring. The mixture was refluxed for 30 minutes. The reaction mixture was poured into a diluted hydrochloric acid. The mixture was subjected to extraction with dichloromethane. The extract was dried over magnesium sulfate and subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=100/1→50/1) and then recrystallized from dichloromethane-diethyl ether to obtain 1.6 g of 5-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. extractionThe mixture was subjected to extraction with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. distillationsubjected to vacuum distillation
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=100/1→50/1)
  7. customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-7746469717dd40258fff531d5fb7e20e
Source dataset
uspto-grants-1997_04
Patent number
US05622947

Linked notes

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