Iodoethane → HCID 22506169, compound

HRID 1814414Notes

Reaction equation

HRID 1814414 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](I)[CH3:32]>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:31][CH3:32])[CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22506255HCID 22506255, compound

Product 1

HCID 22506169HCID 22506169, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of N-[3-[2-(4-chlorophenyl)ethylamino]propyl]phthalimide (2.28 g, 6.65 mmol) and potassium carbonate (1.8 g, 13 mmol) in CH3CN (50 ml) was added ethyl iodide (1.6 ml, 20 mmol). The mixture was stirred at 70° C. for 16 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the residue was chromatographed on silica gel (eluting with 2% methanol/chloroform) to afford N-[3-[[2-(4-chlorophenyl)ethyl](ethyl)amino]propyl]phthalimide (1.41 g, 57%): MS(ES+) m/e 371 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.84 (m, 2H), 7.71 (m, 2H), 7.23 (d, J=8.5 Hz, 2H), 7.11 (d, J=8.5 Hz, 2H), 3.71 (t, J=7.3 Hz, 2H), 2.66 (m, 4H), 2.57 (m, 4H), 1.83 (m, 2H), 1.00 (t, J=7.1 Hz, 3H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum to dryness
  3. customthe residue was chromatographed on silica gel (eluting with 2% methanol/chloroform)

Sources & evidence

ORD record
ord-23b5e99a62f048a09d7b465f506efdd6
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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