Acetyl chloride → 2-(Piperidin-1-yl)acetamide

HRID 1785875Notes

Reaction equation

HRID 1785875 reaction equation
[N:1]1(N)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8]([N:11](C(C)C)CC)(C)[CH3:9].C(Cl)(=[O:19])C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:1]1([CH2:9][C:8]([NH2:11])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 166581-AminopiperidineHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 186182962-(Piperidin-1-yl)acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the piperidine amine obtained above (676 mg, 1.59 mmol) in methylene chloride (25 mL) was added diisopropylethylamine (616 mg, 849 uL, 4.77 mmol), followed by acetyl chloride (162 mg, 156 uL, 2.06 mmol). The mixture was stirred at room temperature over night. The reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted with additional methylene chloride. The extracts were combined, washed with brine, dried over sodium sulfate, filtered, dried and concentrated to afford the piperidine acetamide (844 mg, >100%).

Workup

  1. extractionextracted with additional methylene chloride
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-827d3689fd1b434982c9c48ed847e029
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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