Potassium Carbonate → Ethyl 2-(4-((6-chloropyridin-3-yl)methyl)piperazin-1-yl)acetate

HRID 79206

반응식

HRID 79206 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16]([O:18][C:19]([CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:20])[CH3:17]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:25]2[CH2:24][CH2:23][N:22]([CH2:21][C:19]([O:18][CH2:16][CH3:17])=[O:20])[CH2:27][CH2:26]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 207112Ethyl piperazine-1-acetate

생성물 1

HCID 58300204Ethyl 2-(4-((6-chloropyridin-3-yl)methyl)piperazin-1-yl)acetate수율 30.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred suspension of 2-chloro-5-(chloromethyl)pyridine (2.0 g, 12 mmol) in acetonitrile (60 mL) was added potassium carbonate (1.5 mL, 25 mmol) followed by 1-(ethoxycarbonylmethyl)piperazine (2.0 mL, 12 mmol). The resulting mixture was stirred at room temperature for 19 h. The mixture was filtered through celite and the filter cake was washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was subjected to combi-flash column chromatography (methanol/DCM with Et3N) to give compound 348 (1.1 g, 30% yield) as a colorless liquid. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.31 (1 H, d, J=2.0 Hz), 7.66 (1 H, d, J=6.1 Hz), 7.28 (1 H, d, J=8.1 Hz), 4.18 (2 H, q, J=7.1 Hz), 3.50 (2 H, br. s.), 3.21 (2 H, s), 2.36-2.77 (8 H, m), 1.27 (3 H, t, J=7.2 Hz). LCMS-ESI (POS), M/Z, M+1: Found 298.1.

후처리

  1. filtrationThe mixture was filtered through celite
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-0dda912a2cf9474aba37226729539639
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841312B2

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