Piperidine → 3-Piperidin-1-yl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-propionamide

HRID 643265Notes

Reaction equation

HRID 643265 reaction equation
[CH3:1][C:2]12[CH2:22][CH:6]([N:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])=[CH:13][CH:12]=3)=[O:10])[CH2:8]1)[CH2:5][C:4]([CH3:24])([CH3:23])[CH2:3]2.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CCO>[N:25]1([CH2:20][CH2:19][C:18]([NH:17][C:14]2[CH:13]=[CH:12][C:11]([C:9]([N:7]3[CH2:8][C:2]4([CH3:1])[CH2:22][CH:6]3[CH2:5][C:4]([CH3:24])([CH3:23])[CH2:3]4)=[O:10])=[CH:16][CH:15]=2)=[O:21])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 68429631N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acrylamide

Product 1

HCID 112236473-Piperidin-1-yl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-propionamideYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acrylamide (0.2 g, 0.613 mmol) and piperidine (120 μl, 1.23 mmol) in EtOH (10 ml) was added two drops of TEA. The resulting mixture was heated in a microwave oven at 100° C. for 25 min. The volatiles were evaporated in vacuo and the residue purified on column chromatography (silicagel) using first EtOAc followed by 4% TEA in EtOAc-EtOH 9:1 as eluents. Semi pure fractions were collected, the solvent evaporated in vacuo and the residue dissolved in 1 N HCl (2.5 ml). Water (5 ml) was added followed by diethyl ether (10 ml) and the mixture was stirred for 30 min. The organic phase was discarded and the pH of the aqueous phase adjusted to 10 with 1 N NaOH followed by extraction with diethyl ether (2×10 ml). The combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo affording 55 mg (22%) of the title compound as an oil.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue purified on column chromatography (silicagel)
  3. customSemi pure fractions were collected
  4. customthe solvent evaporated in vacuo
  5. dissolutionthe residue dissolved in 1 N HCl (2.5 ml)
  6. additionWater (5 ml) was added
  7. extractionfollowed by extraction with diethyl ether (2×10 ml)
  8. dry with materialThe combined organic phases were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-29cffb24defb4b92a22594edbba502e2
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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