Dichloromethane → N-[2-[N-ethyl-N-(2-fluoroethyl)amino]ethyl]phthalimide

HRID 2273624Notes

Reaction equation

[CH2:1]([N:3]([CH2:7][CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])[CH2:4][CH2:5]O)[CH3:2].C(N(S(F)(F)[F:26])CC)C.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH2:1]([N:3]([CH2:7][CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])[CH2:4][CH2:5][F:26])[CH3:2]

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of compound 3 (100 mg, 0.38 mmol) in dimethoxyethane (DME, 7 mL) was added at −50° C., under argon, (diethylamino)sulfur trifluoride (DAST, 100 μL, 0.76 mmol). The mixture was stirred at −50° C. for 10 min and then at room temperature for 1.5 h. Dichloromethane (5 mL) and a saturated aqueous sodium carbonate solution (5 mL) were then successively added. The organic layer was dried on magnesium sulfate, filtered and evaporated under vacuum. The residue was chromatographed (SiO2, AcOEt/pentane, 1/1, v/v) to give compound 21 (51 mg, 0.19 mmol) as a white solid. Yield 50%; Rf (SiO2, AcOEt/pentane, 1/1, v/v) 0.53; mp 57-59° C.; IR (KBr) ν 1023, 1403, 1715, 1769, 2700-3000 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.00 (t, 3H, J=7.1 Hz), 2.68 (q, 2H, J=7.1 Hz), 2.86 (m, 4H), 3.78 (t, 2H, J=6.6 Hz), 4.47 (td, 2H, 2JH-F=47.5 Hz, J=5.1 Hz), 7.70 (m, 2H), 7.83 (m, 2H); MS m/z 264 (M+, 1), 104 (100), 76 (38), 56 (18).

Workup

waitat room temperature for 1.5 h
customThe organic layer was dried on magnesium sulfate
filtrationfiltered
customevaporated under vacuum
customThe residue was chromatographed (SiO2, AcOEt/pentane, 1/1

Sources & evidence

ORD record: ord-f77a0a3b9f6f43558fb90ecbbaeb73f7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09125937B2

Reaction notes

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