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

HRID 1195772Notes

Reaction equation

HRID 1195772 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(=O)([O-])[O-].[K+].[K+].Br[CH:25]([CH3:30])[C:26]([O:28][CH3:29])=[O:27]>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:25]([CH3:30])[C:26]([O:28][CH3:29])=[O:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 136404540HCID 136404540, compound

Product 1

HCID 67756055Methyl alpha-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]propionate hydrateYield 86.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-hydroxy-1,2,3,4-tetrahydro-9-acridinamine hydrochloride (3.77 g) in dry dimethylformamide (100 ml) was added potassium carbonate (4.7 g), with stirring. After one hr, methyl 2-bromopropionate (2.51 ml) was added and stirring was continued overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated, and the residue was flash chromatographed (ethyl acetate, then 5% triethylamine/ethyl acetate) to yield 4.05 g (86.7%) of methyl α-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]propionate hydrate.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed (ethyl acetate

Sources & evidence

ORD record
ord-004f083ef6424417bd8f56f309ec82ba
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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