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

HRID 419361ノート

反応式

HRID 419361 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4902982dbb5f477aad256244277cc050
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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