Potassium Carbonate → HCID 54349271, compound

HRID 1603153Notes

Reaction equation

HRID 1603153 reaction equation
[CH3:1][NH:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1.[CH3:32][N:33]([CH3:38])[C:34](=[O:37])[CH2:35]Cl.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][N:2]([CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1)[CH2:35][C:34]([N:33]([CH3:38])[CH3:32])=[O:37]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 10716676HCID 10716676, compound

Product 1

HCID 54349271HCID 54349271, compoundYield 6.9%

Procedure

A mixture of 5-methylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.6 g), N,N-dimethyl-2-chloroacetamide (0.19 g) and potassium carbonate (0.22 g) is refluxed for 24 hours. The reaction solution is concentrated and water is added to the resulting residue. The mixture is extracted three times with dichloromethane. The extract is washed with saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=30:1) to give 5-[N-methyl-N-(dimethylaminocarbonylmethyl)amino]-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.05 g) as colorless amorphous.

Workup

  1. temperatureis refluxed for 24 hours
  2. concentrationThe reaction solution is concentrated
  3. additionwater is added to the resulting residue
  4. extractionThe mixture is extracted three times with dichloromethane
  5. washThe extract is washed with saturated saline solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-dc9c0b8cc07b4251b50e0f9acd0db58b
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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