Potassium Carbonate → 1-(5-Ethynylpyridin-2-yl)-4-methylpiperazine

HRID 1466263ノート

反応式

HRID 1466263 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][Si](C)(C)C)=[CH:16][N:15]=2)[CH2:10][CH2:9]1>CO>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([CH3:7])[CH2:9][CH2:10]2)=[N:15][CH:16]=1)#[CH:21]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 667304181-Methyl-4-(5-((trimethylsilyl)ethynyl)pyridin-2-yl)piperazine

生成物 1

HCID 866588281-(5-Ethynylpyridin-2-yl)-4-methylpiperazine収率 99.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Potassium carbonate (1M aq., 1.5 mL, 1.5 mmol) was added in a drop-wise manner to a solution of 1-methyl-4-(5-((trimethylsilyl)ethynyl)pyridin-2-yl)piperazine (325 mg, 1.19 mmol) in MeOH (5.0 mL) at room temperature, and the resulting mixture was stirred for 2 h. After removal of the solvent in vacuo, water (5 mL) and brine (10 mL) were added and the product was extracted with DCM (150 mL, then 3×10 mL). The combined organic layers were washed with brine (15 mL), dried over Na2SO4 and filtered. Evaporation of the solvent gave 1-(5-ethynylpyridin-2-yl)-4-methylpiperazine (239 mg, quantitative yield), which was used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ ppm 8.32 (s, 1 H), 7.55 (dd, J=8.9, 2.1 Hz, 1 H), 6.58 (d, J=8.8 Hz, 1 H), 3.54-3.67 (m, 4 H), 3.08 (s, 1 H), 2.46-2.58 (m, 4 H), 2.35 (s, 3 H); MS ESI [M+H]+ 201.9, calcd for [C12H15N3+H]+ 202.1.

後処理

  1. customAfter removal of the solvent in vacuo, water (5 mL) and brine (10 mL)
  2. additionwere added
  3. extractionthe product was extracted with DCM (150 mL
  4. washThe combined organic layers were washed with brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-612f5d61895042cfa02f990768f7b877
出典データセット
uspto-grants-2015_04
特許番号
US08999968B2

反応ノート

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