Acridine Orange Base → 10-N(10-Hydroxy-1-decyl)-3,6 bis(dimethylamino)acridine bromide salt
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=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).