Hydrochloric Acid → 7-(4-ethoxyphenyl)-N-[4-[N-methyl-N-(4-oxocyclohexyl)aminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide

HRID 1978557Notes

Reaction equation

HRID 1978557 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:19](=[O:21])(=[O:20])[CH2:18][CH2:17][C:16]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][N:32]([CH:34]5[CH2:39][CH2:38][C:37]6(OCC[O:40]6)[CH2:36][CH2:35]5)[CH3:33])=[CH:27][CH:26]=4)=[O:23])=[CH:15][C:14]=3[CH:44]=2)=[CH:6][CH:5]=1)[CH3:2].Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:19](=[O:21])(=[O:20])[CH2:18][CH2:17][C:16]([C:22]([NH:24][C:25]4[CH:26]=[CH:27][C:28]([CH2:31][N:32]([CH3:33])[CH:34]5[CH2:39][CH2:38][C:37](=[O:40])[CH2:36][CH2:35]5)=[CH:29][CH:30]=4)=[O:23])=[CH:15][C:14]=3[CH:44]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21995979HCID 21995979, compound

Product 1

HCID 219959207-(4-ethoxyphenyl)-N-[4-[N-methyl-N-(4-oxocyclohexyl)aminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamideYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(4-ethoxyphenyl)-N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (140 mg) in THF (20 ml) was added at room temperature 3N hydrochloric acid (1 ml), and the mixture was stirred for 40 hours. To the mixture was added saturated sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give colorless solid, which was recrystallized from ethyl acetate/hexane to give colorless crystals of 7-(4-ethoxyphenyl)-N-[4-[N-methyl-N-(4-oxocyclohexyl)aminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 19) (101.1 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give colorless solid, which
  6. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-95fe5b75bec341a193b03d81d3f9faba
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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