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

HRID 5588

Reaction equation

HRID 5588 reaction equation
C([O:3][C:4]([CH2:6][O:7][CH:8]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]([C:20](=[O:37])[C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:36])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])=[CH:23][CH:22]=2)[CH2:11][CH2:10][CH2:9]1)=O)C.[BH4-].[Li+].Cl>O1CCCC1>[OH:3][CH2:4][CH2:6][O:7][CH:8]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]([C:20](=[O:37])[C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:36])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])=[CH:23][CH:22]=2)[CH2:11][CH2:10][CH2:9]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

To a solution of 5-ethoxycarbonylmethoxy-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (2.2 g) in tetrahydrofuran (50 ml) is added with stirring lithium borohydride (0.28 g) at room temperature, and the mixture is refluxed for 30 minutes. The reaction solution is poured into diluted hydrochloric acid and extracted with dichloromethane. The extract is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=100:1→50:1), and recrystallized from dichloromethane/diethyl ether to give 5-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.6 g) as white powder, mp. 185°-187.5° C.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract is dried over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=100:1→50:1)
  6. customrecrystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-afa3792d8ff0460690d319722a9ee47e
Source dataset
uspto-grants-1993_09
Patent number
US05244898

Linked notes

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