Tetrahydrofuran → 5-ethoxycarbonylmethyl-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 54750

Reaction equation

HRID 54750 reaction equation
O1CCCC1.[CH2:6]([O:8][C:9]([CH:11]=[C:12]1[C:18]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=2[N:16]([C:24](=[O:42])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[CH:27][C:26]=2[CH3:41])[CH2:15][CH2:14][CH2:13]1)=[O:10])[CH3:7].[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.CO>[CH2:6]([O:8][C:9]([CH2:11][CH:12]1[C:18]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=2[N:16]([C:24](=[O:42])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[CH:27][C:26]=2[CH3:41])[CH2:15][CH2:14][CH2:13]1)=[O:10])[CH3:7]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 542377055-ethoxycarbonylmethylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 189173165-ethoxycarbonylmethyl-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineYield 43.2%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

In 30 ml of a 1:1 mixture of tetrahydrofuran and methanol were dissolved 0.30 g of 5-ethoxycarbonylmethylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine and 0.55 g of nickel chloride hexahydrate. Thereto was slowly added 0.26 g of sodium borohydride with ice-cooling and stirring. The mixture was stirred for 10 minutes with ice-cooling. The resulting insolubles were removed by filtration with Celite. The filtrate was concentrated. The residue was purified by silica gel column chromatography (elutant: ethyl acetate/n-hexane=1/1) to obtain 0.13 g of 5-ethoxycarbonylmethyl-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 10 minutes with ice-
  3. temperaturecooling
  4. customThe resulting insolubles were removed by filtration with Celite
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (elutant: ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-82764d1dd4d64f8db9193c7a810375bf
Source dataset
uspto-grants-1997_04
Patent number
US05622947

Linked notes

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