Ethyl Acetate → HCID 15895925, compound

HRID 1870254Notes

Reaction equation

HRID 1870254 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=2[Cl:25])[CH2:9][CH2:8][CH2:7]1)=[O:4].[C:27](=O)([O-])[O-].[Na+].[Na+].C(O[CH2:37][CH3:38])(=O)C>CN(C)C=O>[CH3:1][O:2][C:3]([CH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([NH:24][CH2:27][CH2:37][CH3:38])=[CH:20][C:19]=2[Cl:25])[CH2:9][CH2:8][CH2:7]1)=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 15895924HCID 15895924, compound

Product 1

HCID 15895925HCID 15895925, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 5-methoxycarbonylmethyl-1-(4-amino-2-chlorobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (50 g), n-iodopropane (130 ml) and sodium carbonate (185 g) in dimethylformamide (1.0 liter) is stirred overnight at 60° C. To the mixture is added ethyl acetate, and the mixture is washed with water, dried, concentrated, and purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1) to give 5-methoxycarbonylmethyl-1-(4-n-propylamino-2-chlorobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (30 g) as a white powder.

Workup

  1. washthe mixture is washed with water
  2. customdried
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1)

Sources & evidence

ORD record
ord-ad858626483d4ed8b87b582ce150600f
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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