Morpholine → 4-(1-acetyl-1,2,3,6-tetrahydro-4-pyridinyl)morpholine

HRID 2274941Notes

Reaction equation

HRID 2274941 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([N:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)(=[O:9])[CH3:8]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:1]1([C:13]2[CH2:14][CH2:15][N:10]([C:7](=[O:9])[CH3:8])[CH2:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 122563N-Acetyl-4-piperidone

Product 1

HCID 122092494-(1-acetyl-1,2,3,6-tetrahydro-4-pyridinyl)morpholineYield 100.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

According to Scheme 1, step 1: a mixture of morpholine (67.85 g, 0.779 mol), 1-acetyl-4-piperidone (99.95 g, 0.708 mol) and para-toluenesulfonic acid (0.366 g, 2.1 mmol) in toluene (300 ml) was heated in a Dean-Stark trap apparatus for 16 h at reflux. Solvents were evaporated in vacuo to give 149 g of 1-(4-Morpholin-4-yl-3,6-dihydro-2H-pyridin-1-yl)-ethanone (1) which was used in the next step without any further purification.

Workup

  1. temperaturewas heated in a Dean-Stark trap apparatus for 16 h
  2. temperatureat reflux
  3. customSolvents were evaporated in vacuo

Sources & evidence

ORD record
ord-eacd13c4c90c4276907d0e014090ffb1
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

Loading…