2-Nitro-5-piperidinoaniline → 155198-10-0

HRID 1004588Notes

Reaction equation

HRID 1004588 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([CH:13]=2)[NH2:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:14])=[C:11]([NH2:12])[CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 70622462-Nitro-5-piperidinoaniline

Product 1

HCID 13381914155198-10-0Yield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The nitroaniline derivative (17.0 g, 0.076 mol) (obtained in step 1 above) was hydrogenated using 10% Pd-C (4.0 g) in ethanol (75 mL) by an analogous procedure to that described in preparation 1 (step 4) to yield 4-(piperidin-1-yl)-1, 2-phenylenediamine (13.8 g, 97%) as a viscous oil. IR (Neat) 3390, 1252 cm-1 ; 1H NMR (CDCl3) 6d 1.52 (m, 2H, CH2), 1.70 (t, J=4.7 Hz, 4H, (CH2)2), 2.90 (t, J=5.0 Hz, 4H, N(CH2)2), 3.00 (brs, 4H, 2×NH2), 6.32 (d, J=8.3 Hz, 1H), 6.38 (s, 1H), 6.62 (d, J=8.1 Hz, 1H); Mass (m/z) 191 (M+.).

Workup

  1. customthat described in preparation 1 (step 4)

Sources & evidence

ORD record
ord-44016f359ecd41afa863d2ab33801562
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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