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

HRID 1832149Notes

Reaction equation

HRID 1832149 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 (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 neutralized by the 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, dichloromethane:methanol+1% isopropyl amine) to afford 0.700 g (46.0% yield) of the desired product: 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1H), 7.40 (d, 1H, J=7.8 Hz), 7.24 (t, 1H, J=7.8 Hz), 7.00 (d, 1H, J=7.8 Hz), 3.23–3.14 (m, 5H), 2.82–2.57 (m, 4H) 1.20 (d, 6H, J=6.8 Hz); ESMS m/e: 247.2 (M+H)+; The hydrochloride salt was used for the combustion analysis: Anal. Calc. for C15H22N2O+HCl+0.15 CHCl3: C, 60.51; H, 7.76; N, 9.32. Found: C, 60.57; H, 7.83; N, 8.88.

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 neutralized by the 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, dichloromethane:methanol+1% isopropyl amine)

Sources & evidence

ORD record
ord-5adb75e48561457399cef4e705b25b32
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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