Ethyl Acetate → N-(4-(((7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepin-4-yl)carbonyl)amino)benzyl)-N,N-dimethyl-N-(4-tetrahydropyranyl)ammonium chloride

HRID 566050Notes

Reaction equation

HRID 566050 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:13][CH2:14][O:15][C:16]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=4)=[CH:19][C:17]=3[CH:18]=2)=[O:11])=[CH:5][CH:4]=1.[CH3:32][N:33]([CH3:40])[CH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(OCC)(=O)C>CN(C=O)C>[Cl-:1].[CH2:30]([O:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[CH:21]=[CH:22][C:16]3[O:15][CH2:14][CH2:13][C:12]([C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([CH2:2][N+:33]([CH3:40])([CH3:32])[CH:34]5[CH2:39][CH2:38][O:37][CH2:36][CH2:35]5)=[CH:8][CH:7]=4)=[O:11])=[CH:18][C:17]=3[CH:19]=2)=[CH:24][CH:25]=1)[CH3:31]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10176150N,N-Dimethyltetrahydro-2H-pyran-4-amineHCID 18472558N-(4-chloromethylphenyl)-7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Product 1

HCID 15480022N-(4-(((7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepin-4-yl)carbonyl)amino)benzyl)-N,N-dimethyl-N-(4-tetrahydropyranyl)ammonium chlorideYield 41.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-chloromethylphenyl)-7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (2.38 g) in DMF (20 ml) was added N,N-dimethyl-N-tetrahydropyran-4-ylamine (1.42 g) at room temperature, and the mixture was stirred for 14 hours. To the reaction mixture was added ethyl acetate (100 ml) to precipitate crystals, which were collected by filtration. The crystal was washed with ethyl acetate to give crude product as pale yellow crystals, which were recrystallized from ethanol to give as N-(4-(((7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepin-4-yl)carbonyl)amino)benzyl)-N,N-dimethyl-N-(4-tetrahydropyranyl)ammonium chloride (Compound 250) (1.29 g) colorless crystals.

Workup

  1. customto precipitate crystals, which
  2. filtrationwere collected by filtration
  3. washThe crystal was washed with ethyl acetate
  4. customto give crude product as pale yellow crystals, which
  5. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-949789ce1a5344998abc25945bbe39a0
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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