Ethyl bromoacetate → Ethyl[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]acetate

HRID 1195762Notes

Reaction equation

HRID 1195762 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[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OCC)(=O)C>CN(C)C=O.O>[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][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 136404540HCID 136404540, compound

Product 1

HCID 20068607Ethyl[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]acetateYield 72.91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8-Hydroxy-1,2,3,4-tetrahydro-9-acridinamine hydrochloride (18.07 g) was suspended in 500 ml of dry dimethylformamide. Potassium carbonate (22.6 g) was added, and the reaction mixture was stirred vigorously for 30 mins. Ethyl bromoacetate (18.0 g) was added dropwise, and the reaction was stirred vigorously overnight. The reaction mixture was distributed between ethyl acetate and water, and the organic layer was separated. The aqueous phase was extracted three times with ethyl acetate, and the combined organic phase was washed with water, dried, filtered, and the filtrate evaporated. The residue was purified by flash chromatography (ethyl acetate, then 5% triethylamine/ethyl acetate) to give 15.75 g (72.91%) of product, mp 141°-142° C.

Workup

  1. stirringthe reaction was stirred vigorously overnight
  2. customthe organic layer was separated
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. washthe combined organic phase was washed with water
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate evaporated
  8. customThe residue was purified by flash chromatography (ethyl acetate

Sources & evidence

ORD record
ord-5622e0d3c3d64777a61c1234583bb1e5
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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