Potassium Hydroxide → HCID 13935149, compound

HRID 1904719Notes

Reaction equation

HRID 1904719 reaction equation
[OH-].[K+].[NH2:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2.[O:19]([CH2:26][CH2:27][CH2:28]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[O:19]([CH2:26][CH2:27][CH2:28][NH:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 68522Benzene, (3-bromopropoxy)-HCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13935149HCID 13935149, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

In 600 ml of toluene and 400 ml of 30% potassium hydroxide were combined 10.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one, 39 ml of 3-phenoxypropyl bromide and 3.2 g of tetrabutylammonium hydrogen sulfate catalyst. The biphasic mixture was refluxed (bp 90° C.) with mechanical stirring for 5 hours, during which the reaction went to completion. The organic phase was separated, washed with ice cold saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. The oil was flash chromatographed (silica, ethyl acetate) and the product-containing fractions were combined and evaporated to an oil. Trituration with ether yielded the product as a solid which was recrystallized from dichloromethane/hexane to yield 4.45 g of product, mp 104°-106° C.

Workup

  1. temperatureThe biphasic mixture was refluxed (bp 90° C.)
  2. customThe organic phase was separated
  3. washwashed with ice cold saturated NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil
  7. customchromatographed (silica, ethyl acetate)
  8. customevaporated to an oil

Sources & evidence

ORD record
ord-fe499f1b7ed44fd791b6fdcd717935de
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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