Water → 4-(N-piperidinomethylcarbonyl-N-methyl-amino)-aniline

HRID 2236447Notes

Reaction equation

HRID 2236447 reaction equation
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[C:3](=[O:11])[CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[NH4+].[Cl-].O>CO.[Fe]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:2]([CH3:1])[C:3](=[O:11])[CH2:4][N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 235071034-(N-piperidinomethylcarbonyl-N-methyl-amino)-nitrobenzene

Product 1

HCID 225696444-(N-piperidinomethylcarbonyl-N-methyl-amino)-anilineYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3.12 g (11.3 mmol) of N-Methyl-N-(4-nitrophenyl)-2-piperidin-1-yl-acetamide, 2.52 g (45.1 mmol) of Fe powder and 2.99 g (56.5 mmol) of NH4Cl in 65 mL of MeOH+25 mL of H2O is stirred and refluxed for 3.5 h. The cooled reaction is filtered, the precipitate is washed with MeOH and the filtrate and wash were combined and evaporated. The residue is redissolved in H2O, neutralized with K2CO3 and extracted with EtOAc. The combined extracts were treated with Darco, dried (MgSO4), evaporated and dried in vacuo to give 2.36 g (85%) of brown oil. 1H NMR (DMSO-d6 δ 6.85 (d, 2H, J=7.1 Hz), 6.51 (d, 2H, J=7.1 Hz), 3.30 (s, 2H), 2.78 (s, 3H), 2.24 (s, 4H), 1.50 (m, 6H); MS (ESI) m/z 248.0 (M+H).

Workup

  1. temperaturerefluxed for 3.5 h
  2. customThe cooled reaction
  3. filtrationis filtered
  4. washthe precipitate is washed with MeOH
  5. washthe filtrate and wash
  6. customevaporated
  7. dissolutionThe residue is redissolved in H2O
  8. extractionextracted with EtOAc
  9. additionThe combined extracts were treated with Darco
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customdried in vacuo

Sources & evidence

ORD record
ord-8f315c8c5fe9421bb0f373457d3f2b4b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…