Triphenylphosphine → 5-(3-Nitro-phenoxy)-pentylamine

HRID 217666Notes

Reaction equation

HRID 217666 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[N+:16]([C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][NH2:1])([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 866252691-(5-Azido-pentyloxy)-3-nitro-benzene

Product 1

HCID 690096135-(3-Nitro-phenoxy)-pentylamineYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-azido-pentyloxy)-3-nitro-benzene (3.12 g, 12.5 mmol) in 50 mL THF and 1 mL H2O was added triphenylphosphine (3.27 g, 12.5 mmol). The reaction mixture was stirred at room temperature for 48 hours and then was partitioned with ethyl acetate and water. The aqueous solution was extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with brine, dried over MgSO4, and concentrated to give a yellow liquid, which was purified by silica gel column chromatography to give 5-(3-nitro-phenoxy)-pentylamine (2.75 g, 12.3 mmol, 98%) as a yellow liquid.

Workup

  1. customwas partitioned with ethyl acetate and water
  2. extractionThe aqueous solution was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow liquid, which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a1ee6c77ed174b35ba0cfdc90d934db9
Source dataset
uspto-grants-2012_06
Patent number
US08198284B2

Reaction notes

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