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

HRID 2409854노트

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HRID 2409854 반응식
[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]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 660341,2-Ethanediamine, N1,N1-diethyl-N2-methyl-HCID 742344-(Chloromethyl)benzoic acid

생성물 1

HCID 548860664-(((2-(Diethylamino)ethyl)(methyl)amino)methyl)benzoic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-01b74754d54b4e65babc45420670b600
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815910B2

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