Bromobenzene → 6-Phenylhexan-1-amine

HRID 984629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984629
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1O.BrC1C=CC=CC=1.[CH2:25]([NH2:31])[CH2:26][CH2:27][CH2:28][CH2:29]C.CCCCCCCCCCCC>[Cu]I.O.C(OCC)C.CN(C=O)C>[C:12]1([CH2:16][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][NH2:31])[CH:11]=[CH:10][CH:15]=[CH:14][CH:13]=1

Komponenten

10

Edukt 5

HCID 7961BromobenzeneHCID 8102HexylamineHCID 8182DodecaneHCID 113352,6-DimethylphenolHCID 62657Potassium Phosphate, Tribasic

Produkt 1

HCID 1455586-Phenylhexan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Copper (I) iodide (10 mg, 0.05 mmol, 5 mol %), anhydrous fine powder potassium phosphate (425 mg, 2.0 mmol) and 2,6-dimethylphenol (24 mg, 0.2 mmol, 20 mol %) were put into a screw-capped test tube with a Teflon septum. The tube was evacuated and back-filled with argon (3 cycles). Anhydrous DMF (1.0 mL), bromobenzene (105 μL, 1.0 mmol) and n-hexylamine (158 μL, 1.2 mmol) were added by micro-syringe at room temperature. The reaction mixture was heated at 100° C. for 18 hours. The reaction mixture was then allowed to reach room temperature. Diethyl ether (2 mL), water (2 mL) and dodecane (internal standard, 227 μL) were added. The organic layer was analyzed by GC to give 48% GC yield of N-phenylhexylamine.

Aufarbeitung

  1. customThe tube was evacuated
  2. additionback-filled with argon (3 cycles)
  3. customto reach room temperature

Quellen und Nachweise

ORD-Eintrag
ord-1ca3349703404df1b7914c9b5ca6f201
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867298B2

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