Piperidine → 4-(N-piperidinomethylcarbonyl-N-methyl-amino)-nitrobenzene

HRID 2236446Notes

Reaction equation

HRID 2236446 reaction equation
Br[CH2:2][C:3]([N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:4].CCN(CC)CC.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[CH3:15][N:5]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[C:3](=[O:4])[CH2:2][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 226683752-bromo-N-methyl-N-(4-nitrophenyl)acetamide

Product 1

HCID 235071034-(N-piperidinomethylcarbonyl-N-methyl-amino)-nitrobenzeneYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.82 g (10.3 mmol) of 2-Bromo-N-methyl-N-(4-nitrophenyl)-acetamide and 2.08 g (20.6 mmol) of Et3N in 30 mL of CH2Cl2 at 0° C. under N2 is treated with 0.875 g (10.3 mmol) of piperidine for 5 min at 0° C. and refluxed for 1.25 h. The cooled reaction mixture is washed with H2O, treated with Darco, dried (MgSO4) and evaporated to give 3.00 g (100%) of brown oil. 1H NMR (DMSO-d6) δ 8.25 (d, 2H, J=6.9 Hz), 7.63 (d, 2H, J=6.9 Hz), 3.30 (s, 3H), 3.09 (s, 2H), 2.25 (s, 4H), 1.31 (m, 6H); MS (ESI) m/z 278.0 (M+H).

Workup

  1. temperaturerefluxed for 1.25 h
  2. customThe cooled reaction mixture
  3. washis washed with H2O
  4. additiontreated with Darco
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-1acc86bd8e3f4c02a3fd63e0c6b8860e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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