Hydrochloric Acid → HCID 22500834, compound

HRID 1176126Notes

Reaction equation

HRID 1176126 reaction equation
Cl.C([N:9]1[CH2:14][CH2:13][C:12]([NH:17][S:18]([C:21]2[S:22][C:23]([Cl:26])=[CH:24][CH:25]=2)(=[O:20])=[O:19])([CH2:15][OH:16])[CH2:11][CH2:10]1)(OC(C)(C)C)=O.CCOC(C)=O.CCCCCC>CCOC(C)=O.C(OCC)C>[OH:16][CH2:15][C:12]1([NH:17][S:18]([C:21]2[S:22][C:23]([Cl:26])=[CH:24][CH:25]=2)(=[O:19])=[O:20])[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 22500714HCID 22500714, compound

Product 1

HCID 22500834HCID 22500834, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

4N HCl (5 mL) was added to a stirred solution of N-[1-Boc-4-(hydroxymethyl)piperidin-4-yl]-5-chlorothiophene-2-sulfonamide 5 (0.7 g, 1.7 mmol) in EtOAc (4 mL). The solution was allowed to stir at 25° C. After 30 min, a cloudy solution formed. After 2 h a precipitate formed. TLC (1:1 EtOAc-hexane) indicated the reaction was complete. The solvent was reduced to ˜2-3 mL, diluted with diethyl ether (6 mL) and filtered through a filter funnel. The precipitate was washed with diethyl ether (3×5 mL) to obtain N-[4-(hydroxymethyl)piperidin-4-yl]-5-chlorothiophene-2-sulfonamide as an amorphous white solid (0.48 g, 90.7%). Mass Spectrum (+ESI): 311 (M+H)+.

Workup

  1. customa cloudy solution formed
  2. customAfter 2 h a precipitate formed
  3. filtrationfiltered through a filter funnel
  4. washThe precipitate was washed with diethyl ether (3×5 mL)

Sources & evidence

ORD record
ord-035b13c4424c40e1bf8e8205d6111a32
Source dataset
uspto-grants-2010_11
Patent number
US07842718B2

Reaction notes

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