Hydrochloric Acid → HCID 21715706, compound

HRID 1277231Notes

Reaction equation

HRID 1277231 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[O:19][CH2:18][CH2:17][C:16]([C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][N:30]([CH:32]5[CH2:37][CH2:36][C:35]6(OCC[O:38]6)[CH2:34][CH2:33]5)[CH3:31])=[CH:25][CH:24]=4)=[O:21])=[CH:15][C:14]=3[CH:42]=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[O:19][CH2:18][CH2:17][C:16]([C:20]([NH:22][C:23]4[CH:24]=[CH:25][C:26]([CH2:29][N:30]([CH3:31])[CH:32]5[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]5)=[CH:27][CH:28]=4)=[O:21])=[CH:15][C:14]=3[CH:42]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 18472454HCID 18472454, compound

Product 1

HCID 21715706HCID 21715706, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(4-ethoxyphenyl)-N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-2,3-dihydro-1-benzoxepine-4-carboxamide (151.5 mg) in THF (10 ml) was added at room temperature 3N hydrochloric acid (2 ml), and the mixture was stirred for 22 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 and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated to give colorless solid, which was recrystallized from ethyl acetate/diisopropylether to give colorless crystals of 7-(4-ethoxyphenyl)-N-[4-[N-methyl-N-(4-oxocyclohexyl) aminomethyl]phenyl]-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 288) (103.5 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. concentrationUnder reduced pressure, the mixture was concentrated
  5. customto give colorless solid, which
  6. customwas recrystallized from ethyl acetate/diisopropylether

Sources & evidence

ORD record
ord-4dde9e9f03314094a5e9d638ea3593a8
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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