Acridine Orange Base → 10-N(10-Hydroxy-1-decyl)-3,6 bis(dimethylamino)acridine bromide salt

HRID 565176

Reaction equation

HRID 565176 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:4]=[CH:5][C:6]2[C:15]([CH:16]=1)=[N:14][C:13]1[C:8](=[CH:9][CH:10]=[C:11]([N:17]([CH3:19])[CH3:18])[CH:12]=1)[CH:7]=2.[OH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][Br:32]>CN(C=O)C>[Br-:32].[OH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N:17]([CH3:19])[CH3:18])[CH:12]=2)[CH2:7][C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:20])[CH3:1])=[CH:16][C:15]1=2

Participants

4

Reactant 2

HCID 62344Acridine Orange Base2×HCID 1045071-Decanol, 10-bromo-

Product 1

HCID 8675334110-N(10-Hydroxy-1-decyl)-3,6 bis(dimethylamino)acridine bromide salt

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,6-bis(dimethylamino)acridine (1.0 millimole) is dissolved in DMF (100 mL) containing 1.1 equivalent of tertiary amine base. To this is added 10-hydroxy-1-bromo decane (1.1 millimole), and the mixture is heated to reflux. When monitoring by TLC shows no remaining 3,6-bis(dimethylamino)acridine, the reaction is cooled and the 10-N-(10-hydroxy-1-decyl)-3,6-bis(dimethylamino)acridine is isolated (0.75 millimoles).

Workup

  1. temperaturethe mixture is heated to reflux
  2. temperaturethe reaction is cooled

Sources & evidence

ORD record
ord-f6ff3aea167649f4b9996cc75b799635
Source dataset
uspto-grants-2001_01
Patent number
US06171859B2

Linked notes

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