Piperidine → HCID 69088302, compound

HRID 2251846Notes

Reaction equation

HRID 2251846 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:15]([CH3:18])([CH3:17])[CH3:16])=[O:4].C([O-])([O-])=O.[K+].[K+].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C1COCC1>[N+:12]([C:10]1[CH:9]=[CH:8][C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:11]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 219613852-bromo-N-(2-tert-butyl-5-nitrophenyl)acetamide

Product 1

HCID 69088302HCID 69088302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Bromo-N-(2-tert-butyl-5-nitro-phenyl)-acetamide (2.58 g, 8.2 mmol) and K2CO3 (2.27 g, 16.4 mmol) were combined in a round bottom flask under N2. THF (100 mL) was added and the mixture cooled to 0° C. under N2. Piperidine (1.05 g, 12.3 mmol) was added to the mixture and the mixture was gradually warmed to RT with stirring overnight. The reaction was quenched by filtering it under vacuum and concentrating the filtrate under reduced pressure. The recovered material was eluted through a column of silica gel with a 5 to 50% EtOAc:Hexanes linear gradient giving a brown solid.

Workup

  1. temperaturethe mixture was gradually warmed to RT
  2. customThe reaction was quenched
  3. filtrationby filtering it under vacuum
  4. concentrationconcentrating the filtrate under reduced pressure
  5. washThe recovered material was eluted through a column of silica gel with a 5 to 50% EtOAc
  6. customHexanes linear gradient giving a brown solid

Sources & evidence

ORD record
ord-423440b27144413686825be83f006dd2
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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