Water → HCID 11740743, compound

HRID 745105Notes

Reaction equation

HRID 745105 reaction equation
CN([CH:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]([C:24](=[O:41])[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][CH:26]=2)[CH2:16][CH2:15][CH2:14]1)CCCOC1CCCCO1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C(O)C>[CH3:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C:32]([NH:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([N:17]2[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:13][CH2:14][CH2:15][CH2:16]2)=[O:41])=[CH:26][CH:27]=1)=[O:40]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 19607827HCID 19607827, compound

Product 1

HCID 11740743HCID 11740743, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-(N-methyl-N-[3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propyl]amino)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.55 g) in ethanol (10 ml) is added pyridinium p-toluenesulfonate (0.03 g) and the mixture is heated at 60° C. overnight. After the mixture is refluxed for more 2 hours, water and pyridinium p-toluenesulfonate (0.03 g) are added thereto. The mixture is refluxed for 4 hours. The reaction solution is concentrated and to the resulting residue is added dichloromethane. The mixture is basified with aqueous sodium hydrogen carbonate solution and 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-IN-methyl-N-(3-hydroxypropyl)amino]-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.26 g) as colorless amorphous.

Workup

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

Sources & evidence

ORD record
ord-8d50502ac0ef46ceb79fd66c61a4a8e7
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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