Dimethylformamide → 1-formyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-7-(4-propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide

HRID 586830Notes

Reaction equation

HRID 586830 reaction equation
[CH:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH3:23])=[CH:16][CH:15]=3)=[CH:13][C:8]=2[CH:7]=[C:6]([C:24](O)=[O:25])[CH2:5][CH2:4]1)=[O:2].S(Cl)(Cl)=O.[CH3:31][N:32]([CH:34]=O)[CH3:33]>>[CH:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH3:23])=[CH:16][CH:15]=3)=[CH:13][C:8]=2[CH:7]=[C:6]([C:24]([NH:3][C:9]2[CH:10]=[CH:11][C:12]([CH2:34][N:32]([CH3:31])[CH:33]3[CH2:22][CH2:21][O:20][CH2:17][CH2:16]3)=[CH:13][CH:8]=2)=[O:25])[CH2:5][CH2:4]1)=[O:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22329207HCID 22329207, compound

Product 1

HCID 223289561-formyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-7-(4-propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamideYield 81%

Procedure

In DMF (10.0 ml) was suspended 1-formyl-7-(4-propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (433 mg). To the suspension was added thionyl chloride (0.22 ml), and the mixture was stirred at room temperature for 30 minutes. Under reduced pressure, the solvent was evaporated, and to the mixture was added THF (15.0 ml). On the other hand, to 4-[[N-methyl-N-tetrahydro-2H-pyran-4-yl)amino]methyl]aniline dihydrochloride (434 mg) was added THF (10.0 ml) and then added triethylamine (1.29 ml). The previously prepared acid chloride suspension was added dropwise at 0° C. The mixture was stirred at room temperature for 4 hours. To the mixture was added water, and the mixture was washed with water and saturated brine, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol to give 1-formyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-7-(4-propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide (554 mg, 81%) as white crystals.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the mixture was added THF (15.0 ml)
  3. additionOn the other hand, to 4-[[N-methyl-N-tetrahydro-2H-pyran-4-yl)amino]methyl]aniline dihydrochloride (434 mg) was added THF (10.0 ml)
  4. additionThe previously prepared acid chloride suspension was added dropwise at 0° C
  5. stirringThe mixture was stirred at room temperature for 4 hours
  6. additionTo the mixture was added water
  7. washthe mixture was washed with water and saturated brine
  8. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-4c715b9e70b248b6ad304d660932ad34
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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