HCID 117716265, compound → HCID 117716327, compound

HRID 1398268Notes

Reaction equation

HRID 1398268 reaction equation
[N+:1]([C:4]1[CH:41]=[CH:40][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=2)=[O:15])=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:36][C:33]1[CH:32]=[CH:31][C:30]([O:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]([O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:41][CH:40]=2)=[O:39])=[CH:35][CH:34]=1

Participants

4

Reactant 1

HCID 117716265HCID 117716265, compound

Product 1

HCID 117716327HCID 117716327, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-(4-Nitrophenoxy)-hexanoic acid 2-{2-[6-(4-nitrophenoxy)-hexanoyloxy]-ethoxy}-ethyl ester (12 g) was dissolved in ethyl acetate (200 ml) in a pressure vessel. 5% Palladium on carbon (50% wet, 3 g) was added and the mixture was stirred under an atmosphere of hydrogen (5 Kg) for 1.5 hours. The catalyst was removed by filtration, and the solvent was distilled off under reduced pressure to obtain the crude product which self crystallized over a period of time in the cold. The final product was slurried in diethyl ether, filtered and dried to give pure 6-(4-aminophenoxy)-hexanoic acid 2-{2-[6-(4-aminophenoxy)-hexanoyloxy]-ethoxy}-ethyl ester (6 g) as off-white powder. The final product was characterized by 1H NMR (CDCl3) δ 1.52 (m, 2H, CH2), 1.65 (m, 4H, 2×CH2), 2.37 (t, 2H, CH2), 3.20 (bs, 2H, NH2), 3.70 (t, 2H, CH2), 3.88 (t, 2H, CH2), 4.24 (t, 2H, CH2), 6.64 (d, 2H, Ar), 6.74 (d, 2H, Ar). The product has a melting point of 56-58° C.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customto obtain the crude product which self
  4. customcrystallized over a period of time in the cold
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-edd1de2d2cf5496d98b84813ca3bff45
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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