Hydrochloric Acid → 2-methyl-N-[3-(4-piperidyl)phenyl]propanamide

HRID 1269136Notes

Reaction equation

HRID 1269136 reaction equation
[C:1]([NH:6][C:7]1[CH:8]=[C:9]([CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].Cl>O1CCOCC1>[CH3:3][CH:2]([CH3:4])[C:1]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16757252HCID 16757252, compound

Product 1

HCID 167572552-methyl-N-[3-(4-piperidyl)phenyl]propanamideYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a stirred solution of 2.20 g (6.50 mmol) of tert-butyl 4-[3-(isobutyrylamino)phenyl]-1-piperidinecarboxylate in 100 ml of 1,4-dioxane at 0° C. was bubbled HCl gas for 10 minutes. The reaction mixture was allowed to warm to room temperature and the bubbling of the HCl gas was continued for 1 hour. The solvent was removed in vacuo, the residue was dissolved in 50 mL of water and was basified to pH=13 by addition of KOH pellets. The aqueous solution was extracted with 3×80 mL of dichloromethane. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, 9:1:0.1=dichloromethane:methanol:isopropyl amine) to afford 0.700 g (46% yield) of the desired product: ESMS m/e: 247.2 (M+H)+.

Workup

  1. customthe bubbling of the HCl gas
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 50 mL of water
  4. additionwas basified to pH=13 by addition of KOH pellets
  5. extractionThe aqueous solution was extracted with 3×80 mL of dichloromethane
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (silica, 9:1:0.1=dichloromethane:methanol:isopropyl amine)

Sources & evidence

ORD record
ord-2afe38c151cc4bbea2a04cb83a9f3d9d
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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