2-Morpholinoethylamine → 3-Methoxy-N-[2-(4-morpholinyl)ethyl]benzenesulfonamide

HRID 1986403Notes

Reaction equation

HRID 1986403 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH2:9])[CH2:3][CH2:2]1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([S:18]([NH:9][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 688754243-Methoxy-N-[2-(4-morpholinyl)ethyl]benzenesulfonamideYield 92%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

2-Morpholinoethylamine (1.75 mL, 13.3 mmol) was added over 10 min to a solution of 3-(methyloxy)benzenesulfonyl chloride (2.5 g, 12.1 mmol) in CH2Cl2 (10 mL) and pyridine (4 mL) and the resulting solution was stirred at rt for 1 h. The mixture was concentrated, dissolved in EtOAc and the organic phase was washed with H2O and brine, dried (MgSO4), filtered and the filtrate was concentrated to give an orange oil (3.3 g, 92%) which was used directly in the next step. MS (ES+) m/e 301 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washthe organic phase was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-19c59fafaec849d6bea2b48ed34ce3f9
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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