Triethylamine → Tert-butyl 4-(2,5-dicyano-3,4,6-trifluorophenyl)piperazine-1-carboxylate

HRID 595015

반응식

HRID 595015 반응식
F[C:2]1[C:9]([F:10])=[C:8]([C:11]#[N:12])[C:7]([F:13])=[C:6]([F:14])[C:3]=1[C:4]#[N:5].[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C>CC(C)=O.O>[C:4]([C:3]1[C:6]([F:14])=[C:7]([F:13])[C:8]([C:11]#[N:12])=[C:9]([F:10])[C:2]=1[N:18]1[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]1)#[N:5]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 15783TetrafluoroterephthalonitrileHCID 143452tert-Butyl piperazine-1-carboxylate

생성물 1

HCID 86671743Tert-butyl 4-(2,5-dicyano-3,4,6-trifluorophenyl)piperazine-1-carboxylate수율 51.2%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
55 °C

실험 절차

2,3,5,6-tetrafluoroterephthalonitrile (1 g, 5 mmol) was dissolved in acetone (15 mL) in a 2-necked flask under Nitrogen. A solution of tert-butyl piperazine-1-carboxylate (1.39 g, 7.5 mmol) in water (3 mL) was then added followed by triethylamine (1.01 g, 10 mmol). The solution was heated to 55° C. for 8 h then cooled to rt. The resulting solid was filtered then washed with acetone. The filtrate was concentrated under vacuum and the residue was dissolved again in DCM (30 mL) and washed once with 1M HCl (30 mL) and once with brine (30 mL). The organics were dried over Na2SO4, filtered and the solvent removed in vacuo to give tert-butyl 4-(2,5-dicyano-3,4,6-trifluorophenyl)piperazine-1-carboxylate as a bright yellow solid (0.938 g, 51% yield).

후처리

  1. temperaturethen cooled to rt
  2. filtrationThe resulting solid was filtered
  3. washthen washed with acetone
  4. concentrationThe filtrate was concentrated under vacuum
  5. dissolutionthe residue was dissolved again in DCM (30 mL)
  6. washwashed once with 1M HCl (30 mL) and once with brine (30 mL)
  7. dry with materialThe organics were dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-0a1c2be596b64a1daf884580694e7663
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242987B2

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