N-2-(4-nitrophenoxy)ethyl-4-(4-nitrophenoxy)piperidine → N-2-(4-aminophenoxy)ethyl-4-(4-aminophenoxy)piperidine

HRID 1656597Notes

Reaction equation

HRID 1656597 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([O:17][C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=3)[CH2:15][CH2:16]2)=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 19788723N-2-(4-nitrophenoxy)ethyl-4-(4-nitrophenoxy)piperidine

Product 1

HCID 19788724N-2-(4-aminophenoxy)ethyl-4-(4-aminophenoxy)piperidineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

N-2-(4-Nitrophenoxy)ethyl-4-(4-nitrophenoxy)piperidine (1.50 g, 3.87 mmol) was hydrogenated in THF/MeOH (1:1, 60 mL) at 50 psi over 10% Pd/C (0.5 g) for 16 hours. The mixture was filtered through solka floc and the filtrate was concentrated. Purification by flash chromatography (8% MeOH/CHCl3) gave 0.97 g (80%) of N-2-(4-aminophenoxy)ethyl-4-(4-aminophenoxy)piperidine as a yellow oil. 1H NMR (DMSO-d6): δ 6.65 (d, 4H), 6.50 (d, 4H), 4.60 (br s, 4H), 4.05 (m, 1H), 3.90 (t, 2H), 2.78 (m, 2H), 2.60 (t, 2H), 2.15 (m, 2H), 1.85 (m, 2H), 1.55 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through solka floc
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash chromatography (8% MeOH/CHCl3)

Sources & evidence

ORD record
ord-f8a9fe69fb3745bc95505f59056e96b9
Source dataset
uspto-grants-1993_10
Patent number
US05254689

Reaction notes

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