Potassium Carbonate → [1-(2-Nitro-5-phenylcarbamoyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester

HRID 1773576Notes

Reaction equation

HRID 1773576 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[C:20]([O:24][C:25](=[O:34])[NH:26][CH2:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:20]([O:24][C:25](=[O:34])[NH:26][CH2:27][CH:28]1[CH2:29][CH2:30][N:31]([C:2]2[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH2:32][CH2:33]1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate2×HCID 566888823-chloro-4-nitro-N-phenyl-benzamide

Product 1

HCID 66664552[1-(2-Nitro-5-phenylcarbamoyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-chloro-4-nitro-N-phenyl-benzamide (0.13 g, 0.47 mmol) in N,N-dimethylformamide (10 mL) were added piperidin-4-ylmethyl-carbamic acid tert-butyl ester (0.12 g, 0.56 mmol) and potassium carbonate (0.1 g, 0.72 mmol) and the resulting mixture was heated at 50° C. overnight. The reaction mixture was then heated at 80° C. for 8 hours; then more piperidin-4-ylmethyl-carbamic acid tert-butyl ester (0.33 mmol) and potassium carbonate (0.14 g, 1 mmol) were added and the resulting mixture was heated at 85° C. overnight. The reaction mixture was partitioned between water and ethyl acetate, the organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified on a silica gel plug (hexane/EtOAc, 20/80 to 40/60) to give 0.13 g, (61% yield) of [1-(2-nitro-5-phenylcarbamoyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester as on orange colored solid.

Workup

  1. temperatureThe reaction mixture was then heated at 80° C. for 8 hours
  2. temperaturethe resulting mixture was heated at 85° C. overnight
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude residue was purified on a silica gel plug (hexane/EtOAc, 20/80 to 40/60)

Sources & evidence

ORD record
ord-c1efb608c4cc4682b588ba54d6f510fb
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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