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Potassium Carbonate → Ethyl alpha-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]butyrate hydrate

HRID 981936
Notes
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Reaction equation

HRID 981936 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 95577Butanoic acid, 2-bromo-, methyl esterHCID 136404540HCID 136404540, compound

Product 1

HCID 67757092Ethyl alpha-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]butyrate hydrate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

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

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionextracted with ethyl acetate (2 l)
  4. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customchromatographed (ethyl, acetate, 5% triethylamine/ethyl acetate)

Sources & evidence

ORD record
ord-82679f9fb56c49248de3067ea0a58cf5
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04994452

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes