碳酸钾 → 4-[(6-氯-3-吡啶基)甲基]-1-哌嗪甲酸叔丁酯

HRID 79201

反应方程式

HRID 79201 反应方程式
[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+].[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[OH-].[Na+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:19]2[CH2:18][CH2:17][N:16]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20]2)=[CH:6][CH:7]=1

参与物

6

反应物 4

HCID 11430碳酸钾HCID 14798二甲基对苯二胺二盐酸HCID 143452N-BOC-哌嗪HCID 1554792-氯-5-氯甲基吡啶

产物 1

HCID 457889934-[(6-氯-3-吡啶基)甲基]-1-哌嗪甲酸叔丁酯收率 84.7%

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂

实验过程

To a stirred suspension of 2-chloro-5-(chloromethyl)pyridine (2.0 g, 12 mmol) in acetonitrile (40 mL) was added potassium carbonate (1.5 mL, 25 mmol) followed by tert-butyl 1-piperazinecarboxylate (2.3 g, 12 mmol). The resulting mixture was stirred at room temperature for 20 h. Upon workup, the mixture was poured into ice and 2 N NaOH aqueous solution and extracted with ethyl acetate (2×). The combined organics were dried over Na2SO4 and concentrated in vacuo. The residue was subjected to combi-flash column chromatography (methanol/DCM) to give compound 339 (3.17 g, 82% yield) as a thick colorless liquid. 1H NMR 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.32 (1 H, d, J=2.0 Hz), 7.66 (1 H, d, J=7.4 Hz), 7.30 (1 H, d, J=8.2 Hz), 3.50 (2 H, s), 3.37-3.47 (4 H, m), 2.38 (4 H, br. s.), 1.46 (9 H, s). LCMS-ESI (POS), M/Z, M+1: Found 312.1.

后处理

  1. extractionextracted with ethyl acetate (2×)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-11d42e68f9ba40d8850ba8553b1c370c
来源数据集
uspto-grants-2014_09
专利号
US08841312B2

关联笔记

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