tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(4-cyano-2-methylphenyl)piperazine-1-carboxylate

HRID 535027ノート

反応式

HRID 535027 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:20]([O:19][C:17]([N:11]1[CH2:16][CH2:15][N:14]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[CH3:10])[CH2:13][CH2:12]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

参加物

5

反応物 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27374944-Bromo-3-methylbenzonitrile

生成物 1

HCID 60051111Tert-butyl 4-(4-cyano-2-methylphenyl)piperazine-1-carboxylate収率 86.9%

試薬・触媒・溶媒 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Part 4: To a nitrogen flushed flask containing PdCl2dppf (65.8 mg, 0.081 mmol), dppf (44.6 mg, 0.081 mmol) and 4-bromo-3-methylbenzonitrile (631 mg, 3.22 mmol) in THF (5 mL) at −78° C. was added tert-butyl 1-piperazinecarboxylate (500 mg, 2.68 mmol) as a solid. The resultant mixture was heated to 100° C. and vigorously stirred overnight under nitrogen. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 0 to 30% ethyl acetate in hexane) to afford 4-(4-cyano-2-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (702 mg, 86.9%). MS (ESI): 302.0 (M+H+).

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (eluting with 0 to 30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-3feaed3d8d6f4ae6b5d7028060ec2ef9
出典データセット
uspto-grants-2014_10
特許番号
US08853243B2

反応ノート

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