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

HRID 989402Notes

Reaction equation

HRID 989402 reaction equation
Br[CH2:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CC(C)=O>[N:22]1([CH2:2][C:3]([N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[CH3:6])=[O:4])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 226683752-bromo-N-methyl-N-(4-nitrophenyl)acetamide

Product 1

HCID 235071034-(N-piperidinomethylcarbonyl-N-methyl-amino)-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.4 g (20 mmol) of 4-(N-bromomethylcarbonyl-N-methyl-amino)-nitrobenzene are dissolved in 100 ml of acetone and combined with 5.5 g (40 mmol) of potassium carbonate. 3 ml (30 mmol) of piperidine are slowly added dropwise and the mixture is stirred for 18 hours at ambient temperature. The reaction solution is filtered, and the filtrate is evaporated to dryness. The residue is dissolved in ethyl acetate, washed with water, dried over magnesium sulphate and evaporated to dryness.

Workup

  1. filtrationThe reaction solution is filtered
  2. customthe filtrate is evaporated to dryness
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-90cf0a2666be46f79316fd37df1bb63e
Source dataset
uspto-grants-2003_10
Patent number
US06638965B2

Reaction notes

Loading…