Morpholine → 4-(6-chloro-pyridine-3-sulfonyl)-morpholine

HRID 2245548Notes

Reaction equation

HRID 2245548 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[Cl:14][C:15]1[N:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>ClCCl>[Cl:14][C:15]1[N:20]=[CH:19][C:18]([S:21]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 2741474-(6-chloro-pyridine-3-sulfonyl)-morpholineYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethylamine (0.27 mL, 1.94 mmol) and morpholine (0.085 mL, 0.97 mmol) in dry dichloromethane (2 mL) was added to a stirred suspension of 6-chloropyridine-3-sulfonyl chloride (0.204 g, 0.96 mmol; described in: Naegeli, C. et al. Helv. Chim. Acta. 1938, 21, 1746-1750) in dry dichloromethane (1 mL). The resulting clear solution was stirred at room temperature for 20 min. The solvent was evaporated and the residue was purified on a silica gel column using dichloromethane/methanol, (97:3), as the eluent to give 0.176 g (70% yield) of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 8.75 (dd, J=3, 1 Hz, 1H), 8.18 (dd, J=8, 3 Hz, 1H), 7.82 (dd, J=8, 1 Hz, 1H), 3.63 (m, 4H), 2.96 (m, 4H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-2b4068c9fabc4358aff4153e6358a7b0
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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