(1,1'-Biphenyl)-2-ol → 6-Phenylhexan-1-amine

HRID 984630Notes

Reaction equation

HRID 984630 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.BrC1C=CC=CC=1.C([NH2:35])CCCCC.CCCCCCCCCCCC>[Cu]I.O.C(OCC)C.C1(C)C=CC=CC=1>[C:9]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:35])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

10

Reactant 5

HCID 7017(1,1'-Biphenyl)-2-olHCID 7961BromobenzeneHCID 8102HexylamineHCID 8182DodecaneHCID 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 1140TolueneSolventHCID 3283Diethyl EtherSolvent

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-phenylphenol (34 mg, 0.2 mmol, 20 mol %) were put into a screw-capped test tube with a Teflon septum. Anhydrous toluene (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 under air atmosphere. The reaction mixture was heated at 100° C. for 22 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 33% GC yield of N-phenylhexylamine.

Workup

  1. customto reach room temperature

Sources & evidence

ORD record
ord-5ceefe466195443c91d935e20ef7fdf3
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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