1,2-Dimethoxyethane → Ammonia

HRID 1266973Notes

Reaction equation

HRID 1266973 reaction equation
[CH3:1][N:2]1[CH:8]2[CH2:9][CH2:10][CH:3]1[CH2:4][NH:5][CH2:6][CH2:7]2.Cl[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([O:18][CH2:19][CH3:20])[CH:17]=1.C[C:22]([CH3:25])([O-:24])C.[K+].[OH-:27].[Na+].C[O:30][CH2:31][CH2:32][O:33]C>>[NH3:2].[C:22]([OH:24])(=[O:30])/[CH:25]=[CH:15]/[C:16]([OH:18])=[O:27].[C:19]([OH:24])(=[O:18])/[CH:20]=[CH:31]/[C:32]([OH:33])=[O:27].[CH2:19]([O:18][C:16]1[CH:17]=[C:12]([N:5]2[CH2:6][CH2:7][CH:8]3[N:2]([CH3:1])[CH:3]([CH2:10][CH2:9]3)[CH2:4]2)[CH:13]=[N:14][CH:15]=1)[CH3:20]

Participants

7

Reactant 5

HCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 115211283-Chloro-5-ethoxypyridineHCID 139737309-Methyl-3,9-diazabicyclo[4.2.1]nonaneHCID 23665647Potassium tert-butoxide

Product 2

HCID 222AmmoniaHCID 698453093-[5-Ethoxy-(3-pyridyl)]-9-methyl-3,9-diazabicyclo-[4.2.1]-nonane bis-fumaric Acid Salt

Procedure

A mixture of 9-methyl-3,9-diazabicyclo-[4.2.1]-nonane (1.50 g, 10.7 mmol), 3-chloro-5-ethoxypyridine (3.38 g, 21.4 mmol), potassium tert-butoxide (2.4 g, 21.4 mmol) and 1,2-dimethoxyethane (20 ml) was stirred at room temperature overnight. Aqueous sodium hydroxide (30 ml, 1 M) was added and the mixture was extracted two times with ethyl acetate (20 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 0.39 g, 21%. Mp. 142-144° C.

Workup

  1. extractionthe mixture was extracted two times with ethyl acetate (20 ml)

Sources & evidence

ORD record
ord-1f517aa4e58c41c19f1de57a157b424a
Source dataset
uspto-grants-2003_04
Patent number
US06552012B2

Reaction notes

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