Methyl 7-(4-piperidinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate → 7-(4-Piperidinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1978587Notes

Reaction equation

[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]4[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25]([O:27]C)=[O:26])=[CH:18][C:17]=4[CH:29]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]4[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25]([OH:27])=[O:26])=[CH:18][C:17]=4[CH:29]=3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 70 °C

Procedure

To methyl 7-(4-piperidinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (600 mg) was added 6N hydrochloric acid (60 ml), and the mixture was stirred at 70° C. for 5 hours and concentrated under reduced pressure. To the residue was added ethanol, and to the mixture were added 8N sodium hydroxide solution and 1N sodium hydroxide solution to make the solution pH 6-7. The mixture was concentrated under reduced pressure to give solid, which was collected by filtration and washed with water, 2-propanol, acetone and diisopropylether to give yellow powder of 7-(4-piperidinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (549.5 mg).

Workup

concentrationconcentrated under reduced pressure
additionTo the residue was added ethanol
additionto the mixture were added 8N sodium hydroxide solution and 1N sodium hydroxide solution
concentrationThe mixture was concentrated under reduced pressure
customto give solid, which
filtrationwas collected by filtration
washwashed with water, 2-propanol, acetone and diisopropylether

Sources & evidence

ORD record: ord-1c0ad464721b4e82a06b1f16ea7a3fe0
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235771B1

Reaction notes

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