Magnesium → (1-Ethyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine
Reaction equation
[Mg].C1(S([N:11]2[C:26]([CH2:27][CH3:28])=[C:15]3[CH2:16][CH:17]([N:23]([CH3:25])[CH3:24])[C:18]4[CH2:19][O:20][CH:21]=[CH:22][C:13]([C:14]=43)=[CH:12]2)(=O)=O)C=CC=CC=1>CO.C(Cl)(Cl)Cl>[CH2:27]([C:26]1[NH:11][CH:12]=[C:13]2[CH:22]=[CH:21][O:20][CH2:19][C:18]3[CH:17]([N:23]([CH3:25])[CH3:24])[CH2:16][C:15]=1[C:14]2=3)[CH3:28]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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.).
Workup
- additionIce was added to the reaction mixture which
- filtrationThe insoluble materials were filtered off through cerite and the filtrate
- extractionwas extracted with chloroform
- washThe extracts were washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue obtained
- customwas chromatographed on aluminum oxide in chloroform:hexane (2:1)
Sources & evidence
- ORD record
- ord-11adae173de748f2a0ddc6a422ff8d39
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06858640B2
Reaction notes
Loading…