Triphenylphosphine → 2-(4-nitrophenoxy)ethanamine

HRID 2399881Notes

Reaction equation

HRID 2399881 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 18173786HCID 18173786, compound

Product 1

HCID 122944662-(4-nitrophenoxy)ethanamineYield 95%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 4-nitro 2-aminoethyl ether (610 mg, 2.93 mmol) from Example 213 in 10 mL of THF/water (9:1 ) was treated with triphenyl phosphine (768 mg, 3.0 mmol) at ambient temperature. After stirring for 3 h, the solvent was removed under vacuum and the residue was purified by flash column chromatography on silica gel (eluant 1:9 methanol/methylene chloride) to give 480 mg (95%) of the title compound: 1H NMR (200 MHz, CD3OD) δ8.18 (d, 2H, J=9Hz), 6.96 (d, 2H, J=9Hz), 4.13 (t, 2H, J=5.5Hz), 3.27 (t, 2H, J=5.5Hz).

Workup

  1. customthe solvent was removed under vacuum
  2. customthe residue was purified by flash column chromatography on silica gel (eluant 1:9 methanol/methylene chloride)

Sources & evidence

ORD record
ord-bbf6c76cc68949f6a4d02ffc6b11cfe9
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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