1-Piperidinesulfonamide → HCID 178464677, compound

HRID 1484454Notes

Reaction equation

HRID 1484454 reaction equation
CS[C:3]([N:7]1[CH2:11][CH:10]([CH2:12][CH3:13])[CH:9]=[N:8]1)=[N:4][CH2:5][CH3:6].[N:14]1([S:20]([NH2:23])(=[O:22])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(#N)C>[CH2:5]([NH:4][C:3]([N:7]1[CH2:11][CH:10]([CH2:12][CH3:13])[CH:9]=[N:8]1)=[N:23][S:20]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:22])=[O:21])[CH3:6]

Participants

4

Reactant 2

HCID 2767411-PiperidinesulfonamideHCID 67359394HCID 67359394, compound

Product 1

HCID 178464677HCID 178464677, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.70 g (1 mol equiv.) 4,N-Diethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 0.61 g (1.05 mol equiv.) piperidine-1-sulfonic acid amide were added to 7 mL acetonitrile, and the reaction mixture was refluxed overnight. Volatiles were removed under reduced pressure, and the residue was taken up in ethyl acetate and extracted with 2N NaOH. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (Et2O:PA=2:1) afforded 1.12 g (96%) piperidine-1-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide. 1H NMR (400 MHz, CDCl3) δ 0.99 (t, J=7.5 Hz, 3H), 1.21 (t, J=7.2 Hz, 3H), 1.45-1.72 (m, 8H), 3.07-3.17 (m, 5H), 3.48-3.57 (m, 2H), 3.73 (dd, J=11.0, 7.7 Hz, 1H), 4.08-4.19 (m, 1H), 6.58 (br.s., 1H), 6.87 (d, J=1.3 Hz, 1H)

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customVolatiles were removed under reduced pressure
  3. extractionextracted with 2N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography on silica gel (Et2O:PA=2:1)

Sources & evidence

ORD record
ord-6efd0b21dcf24e3f85c64f85e7442237
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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