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

HRID 595015

反応式

HRID 595015 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0a1c2be596b64a1daf884580694e7663
出典データセット
uspto-grants-2016_01
特許番号
US09242987B2

関連ノート

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