Diethylamine → 3,6-Bis(4-diethylaminobutoxy)acridine trihydrochloride

HRID 1446922Notes

Reaction equation

HRID 1446922 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:20]([CH:21]=1)=[N:19][C:18]1[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH2:23][CH2:24][CH2:25][CH2:26]Cl)[CH:17]=1)[CH:12]=2.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>>[ClH:2].[ClH:1].[ClH:2].[CH2:28]([N:30]([CH2:31][CH3:32])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:20]([CH:21]=1)=[N:19][C:18]1[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][N:19]([CH2:20][CH3:11])[CH2:18][CH3:17])[CH:17]=1)[CH:12]=2)[CH3:29]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 205534713,6-Bis(4-chlorobutoxy)acridine hydrochloride

Product 1

HCID 205535013,6-Bis(4-diethylaminobutoxy)acridine trihydrochloride

Procedure

A mixture of 2.0 g. of 3,6-bis(4-chlorobutoxy) acridine hydrochloride and 150 ml. of diethylamine is heated in a steel bomb at 100° C. for 24 hours. The excess diethylamine is removed under reduced pressure. The residue is dissolved in 150 ml. of chloroform and this chloroform solution is washed with two 30 ml. portions of saturated aqueous sodium bicarbonate, then dried over sodium sulfate and filtered. The chlorofrom is evaporated and the residue is dissolved in 50 ml. of absolute ethanol. A 10 ml. portion of 6 N hydrochloric acid in isopropanol is added giving the desired product as yellow crystals.

Workup

  1. additionA mixture of 2.0 g
  2. customThe excess diethylamine is removed under reduced pressure
  3. dissolutionThe residue is dissolved in 150 ml
  4. washof chloroform and this chloroform solution is washed with two 30 ml
  5. dry with materialportions of saturated aqueous sodium bicarbonate, then dried over sodium sulfate
  6. filtrationfiltered
  7. customThe chlorofrom is evaporated
  8. dissolutionthe residue is dissolved in 50 ml
  9. additionportion of 6 N hydrochloric acid in isopropanol is added

Sources & evidence

ORD record
ord-a85676bb159f43a2a4936ca80286b5a0
Source dataset
uspto-grants-1982_02
Patent number
US04314061

Reaction notes

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