Potassium Iodide → 3-(((2-(Diethylamino)ethyl)(methyl)amino)methyl)benzoic acid

HRID 625385

반응식

HRID 625385 반응식
[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][NH:6][CH3:7])[CH3:2].Br[CH2:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16].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:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16])[CH3:7])[CH3:2]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 660341,2-Ethanediamine, N1,N1-diethyl-N2-methyl-HCID 2456503-(Bromomethyl)benzoic acid

생성물 1

HCID 665868393-(((2-(Diethylamino)ethyl)(methyl)amino)methyl)benzoic acid수율 48.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

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 (9.1 g, 63.00 mmol, 1.50 equiv, 90%) in N,N-dimethylformamide (500 mL), 3-(bromomethyl)benzoic acid (10 g, 46.51 mmol, 1.00 equiv), potassium carbonate (7.8 g, 56.12 mmol, 1.20 equiv), and potassium iodide (1.55 g, 9.34 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 HPLC eluting with 0.05% TFA in a water/CH3CN gradient. The product was obtained as 6 g (46%) of a white solid. 1H-NMR (300 MHz, CDCl3, ppm): δ 8.01 (m, 1H), 7.89-7.87 (m, 1H), 7.28-7.22 (m, 2H), 3.99 (s, 2H), 2.97-2.72 (m, 8H), 2.28 (s, 3H), 1.13-1.01 (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 HPLC
  5. washeluting with 0.05% TFA in a water/CH3CN gradient

출처 및 근거

ORD 기록
ord-caf790e52b57421fbc5fcb5407053606
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09301951B2

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