1,4-Dioxane → Ammonia

HRID 2075781Notes

Reaction equation

HRID 2075781 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:8][NH:7][CH2:6][CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.Br[C:13]1[CH:14]=[CH:15][C:16]([Cl:21])=[C:17]([O:19][CH3:20])[CH:18]=1.CC(C)([O-])C.[K+].O1CCOCC1>O>[NH3:3].[ClH:21].[Cl:21][C:16]1[CH:15]=[CH:14][C:13]([N:7]2[CH2:6][CH2:5][C:4]([CH3:10])([CH3:9])[NH:3][C:2]([CH3:11])([CH3:1])[CH2:8]2)=[CH:18][C:17]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 27695675-Bromo-2-chloroanisoleHCID 1220403559340-40-8HCID 23665647Potassium tert-butoxide

Product 2

HCID 222AmmoniaHCID 67096137HCID 67096137, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,2,7,7-tetramethyl-[1,4]diazepane (1.1 g, 7.2 mmol) [Ramasseul, Rene; Rassat, Andre; Rey, Paul. Journal of the Chemical Society, Chemical Communications (1976), (3), 83-4], 5-bromo-2-chloroanisole (1.6 g, 7.2 mmol), potassium tertbutoxide (1.6 g, 14.5 mmol), palladacycle (200 mg, 0.21 mmol) and dioxane (20 ml) was stirred at reflux for 5 h. Water (50 ml) was added. The mixture was extracted with diethylether (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 0.50 g (23%). The hydrochloric acid salt was precipitated by stirring the free base in a mixture of concentrated hydrochloric acid (3.2 M) in diethylether. Mp 275-278° C.

Workup

  1. temperatureat reflux for 5 h
  2. extractionThe mixture was extracted with diethylether (3×50 ml)

Sources & evidence

ORD record
ord-7291cb5902fe429f886f65d7887966dd
Source dataset
uspto-grants-2011_04
Patent number
US07923444B2

Reaction notes

Loading…