Morpholine → HCID 86721319, compound

HRID 1777077Notes

Reaction equation

HRID 1777077 reaction equation
Cl[S:2]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[O:18]1[CH2:19][CH2:20][N:15]([S:2]([C:5]2[CH:6]=[N:7][CH:8]=[C:9]([CH:14]=2)[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 545939885-Chlorosulfonyl-nicotinic acid methyl ester

Product 1

HCID 86721319HCID 86721319, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-(chlorosulfonyl)nicotinate (35 mg, 0.149 mmol) was added to the morpholine (25.9 mg, 0.297 mmol) in presence of Potassiumcarbonate (41.1 mg, 0.297 mmol) in THF (8 mL) at room temperature and the reaction mixture was stirred for 12 h at room temperature. The reaction was monitored by TLC, after completion of the reaction, Solvent was removed by vacuum and then compound was purified by column chromatography (2% Methanol/DCM) afforded the product methyl 5-(morpholinosulfonyl)nicotinate (26 mg, 0.090 mmol, 60.5% yield) as a solid. 1HNMR (400 MHz, CDCl3): δ 9.41 (s, 1H), 9.12 (s, 1H), 8.60 (d, 1H, J=2.0 Hz), 4.01 (s, 3H), 3.76 (m, 4H), 3.07 (m, 4H).

Workup

  1. customafter completion of the reaction, Solvent
  2. customwas removed by vacuum
  3. customcompound was purified by column chromatography (2% Methanol/DCM)

Sources & evidence

ORD record
ord-bb535f1e41a24a6c8bed6833d8b610ec
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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