Sulfuric Acid → N-(1-Benzyl-4-methylpiperidin-4-yl)acetamide

HRID 456742Notes

Reaction equation

HRID 456742 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:17].[C:21](#[N:23])[CH3:22]>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:23][C:21](=[O:17])[CH3:22])([CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 108459131-Benzyl-4-methylpiperidin-4-ol

Product 1

HCID 21472469N-(1-Benzyl-4-methylpiperidin-4-yl)acetamide

Conditions

Temperature
20 °C

Procedure

To a solution of 1-benzyl-4-methyl-4-piperidinol obtained in Example 10-1 (3.34 g) in acetonitrile (19 mL) was added dropwise conc. sulfuric acid (16 mL) with cooling on an ice bath. The mixture was warmed to 20° C. and stirred for 15 hrs. After cooling, the reaction mixture was quenched by adding 3N potassium hydroxide solution, and the resulting solution (pH9) was extracted with ethyl acetate three times. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated. The residual solid was triturated with ether to give the title compound as a white powder (3.55 g).

Workup

  1. temperaturewith cooling on an ice bath
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched
  4. additionby adding 3N potassium hydroxide solution
  5. extractionthe resulting solution (pH9) was extracted with ethyl acetate three times
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residual solid was triturated with ether

Sources & evidence

ORD record
ord-597e21cc3be74235bf53325df8f9a119
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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