Hydrochloric Acid → 4-(Piperazin-1-yl)-1lambda6-thiane-1,1-dione dihydrochloride

HRID 2263902Notes

Reaction equation

HRID 2263902 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:22].O1CCOCC1>CO.C(OCC)(=O)C>[ClH:22].[ClH:22].[O:21]=[S:17]1(=[O:20])[CH2:16][CH2:15][CH:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59774789tert-butyl 4-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)piperazine-1-carboxylate

Product 1

HCID 567734904-(Piperazin-1-yl)-1lambda6-thiane-1,1-dione dihydrochlorideYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (8.02 g, 25 mmol) in methanol at 45° C. (150 mL) was added 4 N hydrochloric acid in 1,4-dioxane (100 mmol, 25 mL, Aldrich). The mixture was stirred at 45° C. for 7 h until thin layer chromatography (5% methanol in ethyl acetate) indicated that the reaction was complete. The solvent was removed under reduced pressure to give 1-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-piperazine dihydrochloride as a white solid (7.24 g, 99.5%). LR-MS: 218 [(M+H)+]

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-25f336a2bd854871aef281096926b049
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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