Triethylamine → N-[1-(2-Nitro-phenyl)-piperidin-4-yl]-acetamide

HRID 32879Notes

Reaction equation

HRID 32879 reaction equation
C([O-])(=O)C.[C:5]([NH:8][CH:9]1[CH2:14][CH2:13][NH2+:12][CH2:11][CH2:10]1)(=[O:7])[CH3:6].F[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23].C(N(CC)CC)C>CN(C=O)C>[N+:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:12]1[CH2:13][CH2:14][CH:9]([NH:8][C:5](=[O:7])[CH3:6])[CH2:10][CH2:11]1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzeneHCID 11171677N-piperidin-1-ium-4-ylacetamide acetate

Product 1

HCID 49431108N-[1-(2-Nitro-phenyl)-piperidin-4-yl]-acetamideYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask was added 4-acetylamino-piperidinium acetate (as prepared in the previous step) (800 mg, 4.00 mmol), DMF (40 mL), 2-fluoro-1-nitrobenzene (422 μL, 4.00 mmol), triethylamine (836 μL, 6.00 mmol) and the mixture stirred at RT for 17 h. The solvents were removed in vacuo and the residue was purified by silica gel preparative TLC eluting with dichloromethane/hexane/acetonitrile (47.5/47.5/5 v:v:v) yielded 55 mg (5%) of the title compound as a crystalline orange solid. 1H-NMR (400 MHz, CDCl3): δ 8.18 (m, 1H), 8.09 (br d, 1H, J=7.2 Hz), 7.45 (m, 1H), 6.88 (m, 1H), 6.67 (m, 1H), 4.38 (m, 1H), 3.86-3.74 (m, 1H), 3.32 (m, 1H), 3.07 (m, 1H), 2.14 (s, 3H), 1.67-1.52 (m, 2H).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by silica gel preparative TLC
  3. washeluting with dichloromethane/hexane/acetonitrile (47.5/47.5/5 v:v:v)

Sources & evidence

ORD record
ord-28375016a12c4875b0d43160049a97a2
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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