Hexylamine → 6-Phenylhexan-1-amine

HRID 1883394Notes

Reaction equation

HRID 1883394 reaction equation
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.IC1C=CC=CC=1.[CH2:25]([NH2:31])[CH2:26][CH2:27][CH2:28][CH2:29]C.CCCCCCCCCCCC>[Cu]I.O.C(OCC)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

Participants

9

Reactant 5

HCID 8102HexylamineHCID 8182DodecaneHCID 113352,6-DimethylphenolHCID 11575IodobenzeneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 1455586-Phenylhexan-1-amine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

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). Iodobenzene (112 μL, 1.0 mmol) and n-hexylamine (158 μL, 1.0 mmol) were added by micro-syringe at room temperature. The reaction mixture was heated at 80° C. for 18 Aft 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 41% GC yield of N-phenylhexylamine.

Workup

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

Sources & evidence

ORD record
ord-035b75be9fce45c1a1f90f883f66584a
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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