Morpholine → 4-(5-Fluoro-2-methylphenylsulfonyl)morpholine

HRID 597831Notes

Reaction equation

HRID 597831 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.C(N(CC)CC)C.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 1362865-Fluoro-2-methylbenzenesulphonyl chloride

Product 1

HCID 36815744-(5-Fluoro-2-methylphenylsulfonyl)morpholineYield 81%

Procedure

Following the procedure for Intermediate 1 using 5-fluoro-2-methylbenzenesulfonyl chloride (10.0 g, 48 mmol), triethylamine (13.9 mL, 100 mmol) and morpholine (8.37 g, 96 mmol) gave the title compound as white solid (10.07 g, 81% yield). 1H NMR (300 MHz, CDCl3) δ: 7.58 (1H, dd, J=8.6, 2.7 Hz), 7.27 (1H, dd, J=8.4, 5.1 Hz), 7.15 (1H, td, J=8.1, 2.8 Hz), 3.72-3.68 (4H, m), 3.16-3.13 (4H, m), 2.57 (3H, s). LCMS (M+H) calcd for C11H15FNO3S: 260.07; found: 260.15.

Sources & evidence

ORD record
ord-8473a134dd1e4f4596402709fd388edd
Source dataset
uspto-grants-2011_03
Patent number
US07897593B2

Reaction notes

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