2-Nitro-5-(piperidin-1-yl)benzamide → 2-Amino-5-(piperidin-1-yl)benzamide

HRID 855641Notes

Reaction equation

HRID 855641 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])([O-])=O>CO.C(Cl)Cl.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

5

Reactant 1

HCID 27635642-Nitro-5-(piperidin-1-yl)benzamide

Product 1

HCID 107276062-Amino-5-(piperidin-1-yl)benzamideYield 57.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 2-Nitro-5-piperidin-1-yl-benzamide (948 mg, 4.07 mmol) in Methanol (100 mL) was added Pd/C (10%) followed by H2 (1 ATM). After 10 h, the solution was filtered and concentrated. Flash chromatography (0–5% methanol in methylene chloride) afforded the title compound as a white solid (510 mg, 51% yield). FIA m/z 220.1 (M+H) 218 (M−H)

Workup

  1. filtrationthe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-098476508b25437e865a9cd0286c03b1
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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