Bromobenzene → 6-Phenylhexan-1-amine

HRID 2179215Notes

Reaction equation

HRID 2179215 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.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

Participants

10

Reactant 5

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

Product 1

HCID 1455586-Phenylhexan-1-amine

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °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). 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 PC to give 48% 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-11cbc1ace87944ecb0351f155c7c94dd
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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