Hydrochloric Acid → HCID 21995796, compound

HRID 1978558Notes

Reaction equation

HRID 1978558 reaction equation
C1CO[C:3]2([CH2:8][CH2:7][CH:6]([N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]4[CH2:22][CH2:23][S:24](=[O:42])(=[O:41])[C:25]5[CH:31]=[CH:30][C:29]([C:32]6[CH:37]=[CH:36][C:35]7[O:38][CH2:39][O:40][C:34]=7[CH:33]=6)=[CH:28][C:26]=5[CH:27]=4)=[O:20])=[CH:14][CH:13]=3)[CH3:10])[CH2:5][CH2:4]2)[O:2]1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:39]1[O:38][C:35]2[CH:36]=[CH:37][C:32]([C:29]3[CH:30]=[CH:31][C:25]4[S:24](=[O:41])(=[O:42])[CH2:23][CH2:22][C:21]([C:19]([NH:18][C:15]5[CH:16]=[CH:17][C:12]([CH2:11][N:9]([CH3:10])[CH:6]6[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]6)=[CH:13][CH:14]=5)=[O:20])=[CH:27][C:26]=4[CH:28]=3)=[CH:33][C:34]=2[O:40]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21995793HCID 21995793, compound

Product 1

HCID 21995796HCID 21995796, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-7-(3,4-methylenedioxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (100 mg) in THF (10 ml) was added at room temperature 3N hydrochloric acid (1 ml), and the mixture was stirred for 39 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 were recrystallized from ethyl acetate to give colorless crystals of 7-(3,4-methylenedioxyphenyl)-N-[4-[N-methyl-N-(4-oxocyclohexyl)aminomethyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 21) (56.8 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. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-89f508d6e11a4c24b2bf0795d8f247ac
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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