Hydrochloric Acid → 6-(4-Morpholinyl)-1,2-dihydrospiro[indole-3,3'-thietane]1',1'-dioxide

HRID 1618788Notes

Reaction equation

C([N:4]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:16]=2)[C:6]2([CH2:9][S:8](=[O:11])(=[O:10])[CH2:7]2)[CH2:5]1)(=O)C.Cl.C([O-])(O)=O.[Na+]>CO>[N:18]1([C:15]2[CH:16]=[C:17]3[NH:4][CH2:5][C:6]4([CH2:9][S:8](=[O:10])(=[O:11])[CH2:7]4)[C:12]3=[CH:13][CH:14]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-acetyl-6-(4-morpholinyl)-1,2-dihydrospiro[indole-3,3′-thietane]1′,1′-dioxide (0.046 g, 0.137 mmol) in MeOH (1.367 mL) was added 5.0N HCl solution (0.27 mL, 1.37 mmol). The solution was stirred at 60° C. for 3 h and then it was cooled to rt and poured into saturated aqueous NaHCO3 and extracted with DCM. The organic extracts were dried over MgSO4 and evaporated in vacuo to give 6-(4-morpholinyl)-1,2-dihydrospiro[indole-3,3′-thietane]1′,1′-dioxide as a brown solid. Mass Spectrum (ESI) m/e=295.1 (M+1).

Workup

temperatureit was cooled to rt
extractionextracted with DCM
dry with materialThe organic extracts were dried over MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-66a2b04b67a54bbe9795678e427a0171
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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