Phenylethanolamine → HCID 15906035, compound

HRID 984633Notes

Reaction equation

HRID 984633 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6].I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].C(O)(C)C>[Cl-].[Na+].O.[Cu]I>[C:7]1([CH:5]([OH:6])[CH2:4][NH:3][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 1000PhenylethanolamineHCID 3776IsopropanolHCID 51282-IodotolueneHCID 14798Sodium Hydroxide

Product 1

HCID 15906035HCID 15906035, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A 15 mL screw top test tube fitted with a PTFE septum cap was purged with argon before addition of CuI (5.0 mg, 0.026 mmol, 2.6 mol %), NaOH (83.0 mg, 2.08 mmol), and rac-2-amino-1-phenylethanol (143 mg, 1.04 mmol). 2-Iodotoluene (159 μL, 1.25 mmol) and isopropyl alcohol (1.0 mL) were added, via syringe, under argon. The septum cap was replaced with a solid, Teflon-lined cap and the reaction was stirred magnetically at 90° C. for 48 h. The resulting homogeneous solution was allowed to cool before dilution with 10 mL brine. The reaction mixture was transferred to a separatory funnel and extracted with methylene chloride (3×10 mL). The organics were washed with 0.1 M NaOH (2×10 mL), washed with brine (1×15 mL), dried over MgSO4 and concentrated. The crude material was purified by silica gel chromatography using methylene chloride. The product was obtained as a pale yellow, viscous oil in 92% yield (217.4 mg).

Workup

  1. customcap
  2. customThe septum cap
  3. customlined cap
  4. customThe reaction mixture was transferred to a separatory funnel
  5. extractionextracted with methylene chloride (3×10 mL)
  6. washThe organics were washed with 0.1 M NaOH (2×10 mL)
  7. washwashed with brine (1×15 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe crude material was purified by silica gel chromatography
  11. customThe product was obtained as a pale yellow, viscous oil in 92% yield (217.4 mg)

Sources & evidence

ORD record
ord-f6c74885ea5044dd94116c38db266713
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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