Piperazine → Ammonia

HRID 2182260Notes

Reaction equation

HRID 2182260 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH3:10])[CH:7]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C[C:18]([CH3:21])([O-:20])C.[K+].[OH-:23].[Na+].C[O:26]CCOC>>[NH3:4].[C:18]([OH:20])(=[O:26])/[CH:21]=[CH:5]/[C:6]([OH:8])=[O:23].[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:3]=[N:4][CH:5]=1)[CH3:10]

Participants

7

Reactant 5

HCID 4837PiperazineHCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 115211283-Chloro-5-ethoxypyridineHCID 23665647Potassium tert-butoxide

Product 2

HCID 222AmmoniaHCID 1317246591-(5-Ethoxy-3-pyridyl)piperazine fumaric acid salt

Procedure

A mixture of 3-chloro-5-ethoxypyridine (6.5 g, 45.8 mmol), piperazine (19.7 g, 229 mmol), potassium tert-butoxide (11.2 g, 91.6 mmol) and 1,2-dimethoxyethane (150 ml) was stirred at reflux for 1 h. Aqueous sodium hydroxide (1 M, 100 ml) was added and the mixture was extracted two times with ethyl acetate (150 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 4.6 g, 48%. The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp 160.0-161.2° C.

Workup

  1. temperatureat reflux for 1 h
  2. extractionthe mixture was extracted two times with ethyl acetate (150 ml)

Sources & evidence

ORD record
ord-9e90998730dd40dbb7d5927eda22e5d2
Source dataset
uspto-grants-2005_05
Patent number
US06897219B2

Reaction notes

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