Potassium Carbonate → 4,5,6,7,7a,8-Hexahydro-3bH-3-thia-5-aza-cyclopenta[alpha]indene

HRID 1013398Notes

Reaction equation

C([N:8]1[CH2:16][CH:15]2[CH:11]([CH2:12][C:13]3[CH:19]=[CH:18][S:17][C:14]=32)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(Cl)OC(Cl)=O>ClC(Cl)C>[CH:19]1[C:13]2[CH2:12][CH:11]3[CH:15]([C:14]=2[S:17][CH:18]=1)[CH2:16][NH:8][CH2:9][CH2:10]3

Participants

Conditions

Temperature: 22 °C

Procedure

The product from step f) (409 mg, 1.52 mmol) in dichloroethane (8 ml) was treated with K2CO3 (839 mg, 6.08 mmol) and Ace-Cl (658 μl, 6.08 mmol) at 80° C. for 16 hours. Next, the reaction mixture was filtered, concentrated and the residue was dissolved in anhydrous MeOH (25 ml) and stirred for 1 hour at 22° C. The MeOH was concentrated and triturated with ether producing to give 215 mg (66%) of the subtitle compound as its HCl salt. MS calculated for C10H13NS+H 180, observed 180.

Workup

filtrationNext, the reaction mixture was filtered
concentrationconcentrated
dissolutionthe residue was dissolved in anhydrous MeOH (25 ml)
concentrationThe MeOH was concentrated
customtriturated with ether producing

Sources & evidence

ORD record: ord-41d301ec37e249b583ccc6a26a8df4c8
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981919B2

Reaction notes

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