Potassium Carbonate → Ethyl alpha-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]butyrate hydrate
Reaction equation
Cl.[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]=1[C:15]([NH2:17])=[C:14]1[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]1)=[N:8]2.[C:18](=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26](=[O:31])[CH:27](Br)[CH2:28][CH3:29]>CN(C)C=O.O>[OH2:2].[NH2:17][C:15]1[C:16]2[C:7]([N:8]=[C:9]3[C:14]=1[CH2:13][CH2:12][CH2:11][CH2:10]3)=[CH:6][CH:5]=[CH:4][C:3]=2[O:2][CH:27]([CH2:28][CH3:29])[C:26]([O:25][CH2:24][CH3:18])=[O:31]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 8-hydroxy-1,2,3,4-tetrahydro-9-acridinamine hydrochloride (23.08 g) in dry dimethylformamide was added potassium carbonate (28.75 g), with stirring. After one hr, methyl-2-bromobutyrate (15.89 ml) was added dropwise and stirring was continued overnight. The reaction mixture was diluted with water (1.5 l), and extracted with ethyl acetate (2 l). The organic extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (ethyl, acetate, 5% triethylamine/ethyl acetate) to yield 30.34 g of ethyl α-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]butyrate hydrate.
Workup
- stirringstirring
- waitwas continued overnight
- extractionextracted with ethyl acetate (2 l)
- dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customchromatographed (ethyl, acetate, 5% triethylamine/ethyl acetate)
Sources & evidence
- ORD record
- ord-82679f9fb56c49248de3067ea0a58cf5
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04994452
Reaction notes
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