Methanol → HCID 19607773, compound

HRID 1603134Notes

Reaction equation

HRID 1603134 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.[C:32](=[O:35])([O-])[O-].[K+].[K+].[CH2:38]([CH:40]1[O:42][CH2:41]1)Cl.[CH3:43]O>>[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)[CH2:38][CH:40]1[CH2:41][O:42]1.[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)[CH2:43][CH:32]([OH:35])[CH2:41][O:42][CH3:40]

Participants

6

Reactant 4

HCID 887MethanolHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 10716676HCID 10716676, compound

Product 2

HCID 19607773HCID 19607773, compoundHCID 19607968HCID 19607968, compound

Procedure

To a suspension of 5-methylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (3 g) in methanol (30 ml) are added potassium carbonate (1.5 g) and epichlorohydrine (5.7 ml), and the mixture is refluxed for 3 hours. The solvent is distilled off and to the resulting residue is added water and extracted three times with dichloromethane. The extract is washed with saturated saline solution and dried over magnesium sulfate. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=80:1) to give 5-(N-methyl-N-oxiranylmethylamino)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (C; 1.92 g) and 5-[N-methyl-N-(2-hydroxy-3-methoxypropyl)amino]-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (D; 0.38 g).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. distillationThe solvent is distilled off and to the resulting residue
  3. additionis added water
  4. extractionextracted three times with dichloromethane
  5. washThe extract is washed with saturated saline solution
  6. dry with materialdried over magnesium sulfate
  7. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=80:1)

Sources & evidence

ORD record
ord-14c495278920401bbfef1c650ffb8209
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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