Potassium Carbonate → HCID 21196354, compound

HRID 1066993Notes

Reaction equation

HRID 1066993 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][CH2:4][N:5]([CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30195114-Methyl-4-phenylpiperidineHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 21196354HCID 21196354, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-methyl-4-phenyl piperidine (1.61 g, 9.2 mmol) in 100 mL dioxane was added 3-bromo-N-tert-butoxycarbonyl-propylamine (2.25 g, 9.4 mmol) and K2CO3 (3.48 g, 25.2 mmol) and the resulting suspension was heated to reflux for 10 h. The suspension was allowed to cool, filtered and the solvent was evaporated to obtain yellow residue which was purified by column chromatography (Rf=0.4, 3:1 EtOAc/MeOH) to obtain 3-[4-methyl-4-phenyl-piperidin-1-yl]-N-tert-butoxycarbonyl-propylamine as a yellow oil (2.85 g). It was dissolved in 35 mL of CH2Cl2 and 6.0 mL of trifluoroacetic acid was added with stirring at room temperature under argon atmosphere. After 1 h the solvent was evaporated in vacuo and the residue was basified to pH 10 by adding minimum amount of 1 N KOH solution. The product was extracted with CH2Cl2 (3×35 mL), dried over MgSO4, filtered and the solvent was removed in vacuo to obtain 3-[4-methyl-4-phenylpiperidin-1-yl]propylamine as a viscous yellow oil (1.54 g, 73% for two steps). It was used in the next step without further purification. This step “d” is a representative procedure for putting propylamino tether on any piperidine.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureto reflux for 10 h
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customto obtain yellow residue which
  7. customwas purified by column chromatography (Rf=0.4, 3:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-5e0bb61269a34742827f1c3e59bce318
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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