Reaction #53624

Reaction equation

Magnesium

compound ( 55 )

(2-Benzenesulfonyl-1-ethyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine

→

titled compound

Yield 79.0%

(1-Ethyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine

Yield 79.0%

Solvents

chloroform

methanol

Conditions

Workup

1. 1
   workup.ADDITIONIce was added to the reaction mixture which
2. 2
   FiltrationThe insoluble materials were filtered off through cerite and the filtrate
3. 3
   Extractionwas extracted with chloroform
4. 4
   WashThe extracts were washed with brine
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue obtained
8. 8
   Otherwas chromatographed on aluminum oxide in chloroform:hexane (2:1)

Procedure

Magnesium (turning) 246 mg was added to compound (55) in methanol 9 ml and the mixture was stirred at room temperature for 3 h. Ice was added to the reaction mixture which was diluted with chloroform. The insoluble materials were filtered off through cerite and the filtrate was extracted with chloroform. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform:hexane (2:1) to give the titled compound as a pale yellow oil 97.8 mg. Yield 79%. This was treated with 1 eq. oxalic acid to give the salt, which was recrystallized from ether-methanol to give colorless crystals, m.p. 236-237° C. (dec.).

Source