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Dimethylformamide → 1-(3-Methoxybenzyl)-n-[4-[[n-methyl-n-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 586954
Notes
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Reaction equation

HRID 586954 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:39]=[CH:40][CH:41]=1)[CH2:11][N:12]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH3:35])=[CH:25][CH:24]=3)=[CH:22][C:17]=2[CH:16]=[C:15]([C:36]([OH:38])=O)[CH2:14][CH2:13]1.S(Cl)(Cl)=O>O1CCCC1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:39]=[CH:40][CH:41]=1)[CH2:11][N:12]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH3:35])=[CH:25][CH:24]=3)=[CH:22][C:17]=2[CH:16]=[C:15]([C:36]([NH:12][C:18]2[CH:19]=[CH:20][C:21]([CH2:4][N:2]([CH3:1])[CH:3]3[CH2:31][CH2:30][O:29][CH2:26][CH2:25]3)=[CH:22][CH:17]=2)=[O:38])[CH2:14][CH2:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 697473811-(3-Methoxybenzyl)-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid

Product 1

HCID 223292561-(3-Methoxybenzyl)-n-[4-[[n-methyl-n-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

One droplet of DMF was added to a solution of 1-(3-methoxybenzyl)-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (110 mg) in tetrahydrofuran (10 ml). Then, thionyl chloride (80 mg) was added at 0° C., the temperature was returned to room temperature, and the mixture was stirred under nitrogen atmosphere for 1 hour. The solvent and excess thionyl chloride were evaporated under reduced pressure, the resulting residue was suspended in tetrahydrofuran (25 ml), and the suspension was added to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (60 mg) and triethylamine (273 mg) in tetrahydrofuran (10 ml) at 0° C. The suspension was stirred under nitrogen atmosphere at room temperature for 5 hours, to the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, the resulting residue was separated and purified with silica gel column chromatography (methanol:ethyl acetate=1:8), which was recrystallized from hexane-ethyl acetate to give 1-(3-methoxybenzyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 53) (62 mg) as yellow crystals.

Workup

  1. customwas returned to room temperature
  2. customThe solvent and excess thionyl chloride were evaporated under reduced pressure
  3. additionthe suspension was added to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (60 mg) and triethylamine (273 mg) in tetrahydrofuran (10 ml) at 0° C
  4. stirringThe suspension was stirred under nitrogen atmosphere at room temperature for 5 hours, to the mixture
  5. additionwas added water
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe resulting residue was separated
  11. custompurified with silica gel column chromatography (methanol:ethyl acetate=1:8), which
  12. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-ee3846c507b64fec8334da108087224a
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06936602B1

Reaction notes

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