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

HRID 79206

反応式

HRID 79206 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-0dda912a2cf9474aba37226729539639
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

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