Acetic Anhydride → Methyl 3-(1-acetyl-piperid-4-yl)propionate

HRID 1577843Notes

Reaction equation

HRID 1577843 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>CO>[C:13]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10261546Methyl 3-(piperidin-4-yl)propanoate

Product 1

HCID 20569898Methyl 3-(1-acetyl-piperid-4-yl)propionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[piperid-4-yl]propionate (11 g) and acetic anhydride (35 ml) were heated together on a steam bath for 1 hour. The mixture was cooled and methanol (50 ml) was added to destroy excess anhydride. The solution was evaporated to dryness in vacuo and the residue was partitioned between chloroform (200 ml) and 2 N hydrochloric acid (100 ml) dried (Na2CO3) and evaporated to give methyl 3-[1-acetyl-piperid-4-yl]propionate (13 g) as an oil.

Workup

  1. temperatureThe mixture was cooled
  2. customto destroy excess anhydride
  3. customThe solution was evaporated to dryness in vacuo
  4. customthe residue was partitioned between chloroform (200 ml) and 2 N hydrochloric acid (100 ml)
  5. dry with materialdried (Na2CO3)
  6. customevaporated

Sources & evidence

ORD record
ord-75fefbe931cc4eb6b264b4a7613f3c7f
Source dataset
uspto-grants-1981_09
Patent number
US04289772

Reaction notes

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