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

HRID 535027

Reaktionsgleichung

Reaktionsgleichung von HRID 535027
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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 60051111Tert-butyl 4-(4-cyano-2-methylphenyl)piperazine-1-carboxylateAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3feaed3d8d6f4ae6b5d7028060ec2ef9
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853243B2

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