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

HRID 1466263노트

반응식

HRID 1466263 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-612f5d61895042cfa02f990768f7b877
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999968B2

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