Potassium Carbonate → tert-Butyl 4-(2-fluoroethyl)piperazine-1-carboxylate

HRID 419361노트

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HRID 419361 반응식
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[F:20][CH2:21][CH2:22]I>C1COCC1>[F:20][CH2:21][CH2:22][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 143452tert-Butyl piperazine-1-carboxylate

생성물 1

HCID 21082715tert-Butyl 4-(2-fluoroethyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
85 °C

실험 절차

In a sealed tube, 1,1-dimethylethyl 1-piperazinecarboxylate (10.0 g, 54.0 mmol) was dissolved in 100 mL of THF. K2CO3 (11.2 g, 81.0 mmol) and 1-fluoro-2-iodoethane (11.3 g, 64.8 mmol) were added and the reaction was heated to 85° C. for 16 h. The reaction was cooled to rt and solids were filtered and washed with DCM. The filtrate was concentrated in vacuo being careful not to heat the H2O bath past 30° C. The resulting crude product, 1,1-dimethylethyl 4-(2-fluoroethyl)-1-piperazinecarboxylate was carried on to the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.48 (dt, JHF=47.8 Hz, J=4.9 Hz, 2H), 3.24-3.28 (m, 4H), 2.57 (dt, JHF=28.7, J=4.9 Hz, 2H), 2.31-2.36 (m, 4H), 1.34 (s, 9H).

후처리

  1. temperatureThe reaction was cooled to rt
  2. filtrationsolids were filtered
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated in vacuo
  5. temperatureto heat the H2O bath past 30° C
  6. customThe resulting crude product, 1,1-dimethylethyl 4-(2-fluoroethyl)-1-piperazinecarboxylate was carried on to the next step without further purification

출처 및 근거

ORD 기록
ord-4902982dbb5f477aad256244277cc050
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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