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

HRID 1823832Notes

Reaction equation

HRID 1823832 reaction equation
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:18][CH2:17][C:16]([CH3:20])(O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-:21].[Na+].[C:23](#[N:25])[CH3:24]>>[CH2:6]([N:13]1[CH2:18][CH2:17][C:16]([NH:25][C:23](=[O:21])[CH3:24])([CH3:20])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 108459131-Benzyl-4-methylpiperidin-4-ol

Product 1

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

Procedure

Concentrated sulphuric acid (3 ml) was added dropwise to a solution of 1-benzyl-4-methyl-4-piperidinol (640 mg, 2.56 mmol) in acetonitrile (4 ml) at 0° C. After 1 hour the reaction was cautiously poured onto 2N sodium hydroxide (20 ml), the layers separated and the aqueous extracted with dichloromethane (3×). The combined organic extracts were washed with water, brine, dried (K2CO3), filtered and evaporated under reduced pressure to afford the title compound as a clear oil, 600 mg.

Workup

  1. customthe layers separated
  2. extractionthe aqueous extracted with dichloromethane (3×)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (K2CO3)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-466d75ca1683447e972092ef55989ae5
Source dataset
uspto-grants-2006_05
Patent number
US07041667B1

Reaction notes

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