Ethanol → N-methyl-3-(piperidin-4-yl)propanamide

HRID 1577846Notes

Reaction equation

HRID 1577846 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([O:11]CC)=O)[CH2:3][CH2:2]1.C(O)C.[CH3:17][NH2:18]>>[CH3:17][NH:18][C:9](=[O:11])[CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 10012639Ethyl 3-piperidin-4-ylpropanoate

Product 1

HCID 17979215N-methyl-3-(piperidin-4-yl)propanamide

Procedure

Ethyl 3-(piperid-4-yl)propionate (7 g) (prepared similarly to Preparation 21 A using ethyl alcohol in place of methyl alcohol) was dissolved in ethanolic methylamine (33%, 50 ml) and heated in a stainless steel bomb for 6 hours at 120°. The mixture was then evaporated to dryness in vacuo and the residue partitioned between 2 N NaOH (20 ml) and chloroform (40 ml). The chloroform layer was dried (Na2CO3) and evaporated to give N-methyl-3-(piperid-4-yl)propionamide (6 g) as a crude oil.

Workup

  1. customThe mixture was then evaporated to dryness in vacuo
  2. customthe residue partitioned between 2 N NaOH (20 ml) and chloroform (40 ml)
  3. dry with materialThe chloroform layer was dried (Na2CO3)
  4. customevaporated

Sources & evidence

ORD record
ord-12ed0ba7967045adb1c54f88299c0e4f
Source dataset
uspto-grants-1981_09
Patent number
US04289772

Reaction notes

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