Hydrochloric Acid → cis-2,6-Dimethyl-4-(4-piperazinylphenyl)morpholine

HRID 1816751Notes

Reaction equation

HRID 1816751 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18](C(=O)C)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:3]1.Cl.[OH-].[Na+].ClCCl>C(O)C>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)=[CH:13][CH:14]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 540805081-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]ethanone

Product 1

HCID 69677628cis-2,6-Dimethyl-4-(4-piperazinylphenyl)morpholineYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture 1-[4-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]ethanone (11.37 g) and 1.0 mol/l hydrochloric acid (225 ml) in ethanol (220 ml) was refluxed for 23 hours. The reaction mixture was added to a mixture of 1.0 mol/l sodium hydroxide solution and dichloromethane. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure to give cis-2,6-dimethyl-4-(4-piperazinylphenyl)morpholine (3.64 g).

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationThe magnesium sulfate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-32c120474e334b5f942fc3af8fca638a
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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