2-Nitro-3-(piperidin-1-yl)aniline → 3-(Piperidin-1-yl)benzene-1,2-diamine

HRID 334500Notes

Reaction equation

HRID 334500 reaction equation
[N+:1]([C:4]1[C:10]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O>CO.[Pd]>[N:11]1([C:10]2[CH:9]=[CH:8][CH:7]=[C:5]([NH2:6])[C:4]=2[NH2:1])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 125972682-Nitro-3-(piperidin-1-yl)aniline

Product 1

HCID 867010733-(Piperidin-1-yl)benzene-1,2-diamineYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-nitro-3-(piperidin-1-yl)aniline (CXXII) (1.64 g, 6.9 mmol, 1 eq) and Pd/C (0.50 g) in MeOH (20 mL) was stirred at room temperature under 30 psi H2 overnight. After the starting material was consumed completely, the mixture was filtered through a Celite pad and the filtrate was concentrated in vacuo to give the 3-(piperidin-1-yl)benzene-1,2-diamine (CXXIII) (1.1 g, 5.75 mmol, 76% yield) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ ppm 1.59 (brs, 2H), 1.73 (quin, J=5.6 Hz, 4H), 2.84 (brs, 4H), 3.50 (brs, 4H), 6.52 (dd, J=6.4 Hz, J=1.6 Hz, 1H), 6.59-6.75 (m, 2H); ESIMS found for C11H17N3 m/z 192 (M+H).

Workup

  1. customAfter the starting material was consumed completely
  2. filtrationthe mixture was filtered through a Celite pad
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6763ea91d74e49dcb1e1f943c41bf256
Source dataset
uspto-grants-2014_11
Patent number
US08883822B2

Reaction notes

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