Potassium Carbonate → HCID 2842864, compound

HRID 1777041Notes

Reaction equation

HRID 1777041 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[S:9]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16])(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([S:9]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])(=[O:11])=[O:10])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693814-MethylpiperidineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 2842864HCID 2842864, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-methylpiperidine (180 mg, 1.813 mmol) was added to the 3-(chlorosulfonyl)benzoic acid (200 mg, 0.906 mmol) in presence of Potassiumcarbonate (251 mg, 1.813 mmol) in THF (Volume: 5 ml) at room temperature and the reaction mixture was stirred for 12 h at room temperature. Reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by column chromatography (3% CH3OH/CH2Cl2) afforded the title compound as a solid. 1H NMR (CD3OD, 400 MHz): δ 8.32 (m, 1H), 8.27 (m, 1H), 7.96 (m, 1H), 7.72 (t, 1H, J=8.0 Hz), 3.72 (m, 2H), 2.27 (m, 2H), 1.68 (m, 2H), 1.29 (m, 1H), 1.21 (m, 2H), 0.88 (d, 3H, J=6.4 Hz). ESI-MS: 284.1 [M+H]+

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. customthe solvent was removed by vacuum
  4. customcompound was purified by column chromatography (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-b104317417424302a7767b649216b696
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

Loading…