Potassium Iodide → 4-(((2-(Diethylamino)ethyl)(methyl)amino)methyl)benzoic acid

HRID 2409854Notes

Reaction equation

[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][NH:6][CH3:7])[CH3:2].Cl[CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][N:6]([CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH3:7])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Into a 1000-mL round bottom flask, was placed a solution of N1,N1-diethyl-N2-methylethane-1,2-diamine (10 g, 69.23 mmol, 1.20 equiv, 90%) in N,N-dimethylformamide (500 mL), 4-(chloromethyl)benzoic acid (11.5 g, 67.65 mmol, 1.00 equiv), potassium carbonate (10 g, 71.94 mmol, 3.00 equiv), and potassium iodide (1.95 g, 11.75 mmol, 0.20 equiv). The resulting solution was stirred for 2 h at 90° C. in an oil bath. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product (10 g) was purified by reverse phase chromatography eluting with a water/methanol gradient. This resulted in 5 g (27%) of 4-(((2-(diethylamino)ethyl)(methyl)amino)methyl)benzoic acid as a white solid. 1H-NMR (300 MHz, CDCl3, ppm): δ 8.00 (d, J=8.4 Hz, 2H), 7.39 (d, J=8.1 Hz, 2H), 3.68 (s, 2H), 3.23-3.15 (m, 6H), 2.91 (m, 2H), 2.33 (s, 3H), 1.33-1.27 (m, 6H). MS (ES, m/z): 265 [M+H]+.

Workup

customInto a 1000-mL round bottom flask, was placed
filtrationThe solids were filtered out
concentrationThe resulting mixture was concentrated under vacuum
customThe crude product (10 g) was purified by reverse phase chromatography
washeluting with a water/methanol gradient
customThis resulted in 5 g (27%) of 4-(((2-(diethylamino)ethyl)(methyl)amino)methyl)benzoic acid as a white solid

Sources & evidence

ORD record: ord-01b74754d54b4e65babc45420670b600
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815910B2

Reaction notes

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