Piperazine → Ammonia

HRID 2416596Notes

Reaction equation

HRID 2416596 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-d97b429003f4481ea9e62480d0085164
Source dataset
uspto-grants-2004_11
Patent number
US06825189B1

Reaction notes

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