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

HRID 855640Notes

Reaction equation

HRID 855640 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C>C1COCC1>[N+:11]([C:5]1[CH:4]=[CH:3][C:2]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 186681655-Fluoro-2-nitrobenzamide

Product 1

HCID 27635642-Nitro-5-(piperidin-1-yl)benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-Fluoro-2-nitro-benzamide (850 mg, 4.07 mmol) in THF (100 mL), was added piperdine (381 mg, 4.47 mmol) and diisopropyl ethyl amine (780 mL, 4.07 mmol) and the solution was heated to 70 C in a sealed tube for 12 h. The resulting yellow precipitate was collected to give 2-Nitro-5-piperidin-1-yl-benzamide 948 mg (100% yield) HPLC tr=3.58 min (100%), FIA m/e 250.2(M+H) 248.8 (M−H); 1HNMR (500 MHz, dmso): δ 7.95 (1H, d), 7.85 91H, bs), 7.50 (1H, bs), 6.97 (1H, d), 6.80 (1H, s), 3.50 (4H, m), 1.70–1.50 (6H, m).

Workup

  1. temperaturethe solution was heated to 70 C in a sealed tube for 12 h
  2. customThe resulting yellow precipitate was collected

Sources & evidence

ORD record
ord-428011dd4b864e5ca508d99cd795fb65
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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