Ethyl 4-((2-nitrophenyl)amino)piperidine-1-carboxylate → Ethyl 4-(2-aminoanilino)piperidine-1-carboxylate

HRID 1295770Notes

Reaction equation

HRID 1295770 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 3020732Ethyl 4-((2-nitrophenyl)amino)piperidine-1-carboxylate

Product 1

HCID 13046883Ethyl 4-(2-aminoanilino)piperidine-1-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(2-Nitro-phenylamino)-piperidine-1-carboxylic acid ethyl ester (from step 1 above) was dissolved in methanol then hydrogenated over 10% Pd/C (balloon pressure). The hydrogenation was run until the yellow color turned colorless. It was filtered through a celite pad, and the filtrated evaporated to a reddish brown residue. The residue was triturated with 1% ethyl acetate in hexanes and the solid collected by filtration to give 4-(2-amino-phenylamino)-piperidine-1-carboxylic acid ethyl ester (2.02 g; 77%, 2 steps). 1H NMR (CDCl3) δ 1.27 (t, 3H, J=7.2), 1.4 (m, 2H), 2.05 (m, 2H), 3.0 (m, 2H), 3.4 (m, 4H), 4.1 (m, 4H), 6.7 (m, 4H)

Workup

  1. filtrationIt was filtered through a celite pad
  2. customthe filtrated evaporated to a reddish brown residue
  3. customThe residue was triturated with 1% ethyl acetate in hexanes
  4. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-45013441aae84775a8b55915dc04b96a
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

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