4,4'-(Pentamethylenedioxy)-bis-(nitrobenzene) → 1,5-Bis(p-aminophenoxy)pentane

HRID 982598

Reaction equation

HRID 982598 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>O1CCCC1.[Pd]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 5505304,4'-(Pentamethylenedioxy)-bis-(nitrobenzene)HCID 178418361HCID 178418361, compound

Product 1

HCID 141731,5-Bis(p-aminophenoxy)pentaneYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,5-bis(4-nitrophenoxy)pentane (32.7 grams, 94.4 mmol; prepared as described in Part A of this Example) and Pd/C 10% (1.00 gram, obtained from Aldrich Chemical Co.) was stirred for 20 hours in tetrahydrofuran (400 milliliters) under 200 pounds per square inch of hydrogen gas. The mixture was then filtered over CELITE, and the solvent was removed by evaporation under reduced pressure. The resulting crude solid was recrystallized from ethanol to afford pure 1,5-bis(4-aminophenoxy)pentane (24.4 grams, 85.1 mmol, 90 percent yield) as small colorless crystals: mp 78-79° C.; IR (KBr) 3433, 3353, 3217, 2949, 2868, 1856, 1632, 1511, 1473, 1396, 1228, 1031, 1002, 825, 517 cm−1; 1H NMR (300 MHz, CDCl3) δ6.76 (d, 4H, 3J=8.8 Hz), 6.64 (d, 4H, 3J=8.8 Hz), 3.92 (td, 4H, 3J=6.4 Hz, 4J=1.4 Hz), 3.40 (s, 4H), 1.82 (q, 4H, 3J=6.8 Hz), 1.62 (q, 2H, 3J=6.8 Hz): 13C NMR (75 MHz, CDCl3) δ151.31, 140.06, 116.51, 115.78, 68.58, 29.32, 22.83; MS (FAB, 3-nitrobenzyl alcohol) m/e 286.7; Anal. Calcd for C17H22N2O2: C, 71.30; H. 7.74; N, 9.78. Found: C, 71.11; H, 8.22; N, 9.85.

Workup

  1. customprepared
  2. filtrationThe mixture was then filtered over CELITE
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customThe resulting crude solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-067a3642de9e4207955a397517fe5891
Source dataset
uspto-grants-2005_03
Patent number
US06860928B2

Linked notes

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