Hydrochloric Acid → HCID 21715699, compound

HRID 1387984Notes

Reaction equation

HRID 1387984 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][C:25]5[CH:31]=[CH:30][C:29]([C:32]6[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][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>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([C:29]2[CH:30]=[CH:31][C:25]3[S:24][CH2:23][CH2:22][C:21]([C:19]([NH:18][C:15]4[CH:16]=[CH:17][C:12]([CH2:11][N:9]([CH3:10])[CH:6]5[CH2:5][CH2:4][C:3](=[O:2])[CH2:8][CH2:7]5)=[CH:13][CH:14]=4)=[O:20])=[CH:27][C:26]=3[CH:28]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 18472251HCID 18472251, compound

Product 1

HCID 21715699HCID 21715699, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxamide (130 mg) in THF (15 ml) was added at room temperature 6N hydrochloric acid (1 ml), and the mixture was stirred for 66 hours. To the mixture was added sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine and magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the resulting solid was recrystallized from ethyl acetate/hexane to give pale yellow crystals of 7-(4-methoxyphenyl)-N-[4-[N-methyl-N-(4-oxocyclohexyl)aminomethyl]phenyl]-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 284) (78.3 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine and magnesium sulfate
  3. concentrationUnder reduced pressure, the mixture was concentrated
  4. customthe resulting solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-faa0b6b40af2478783131c2b58cf8058
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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