Diethyl Ether → 9-Benzylamino-7-dodecyl-1,2,3,4-tetrahydroacridine hydrochloride

HRID 274869Notes

Reaction equation

HRID 274869 reaction equation
[Cl:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[C:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:4]=2.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCOCC.[OH-].[Na+]>C1(O)C=CC=CC=1>[ClH:1].[CH2:28]([NH:35][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[C:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:4]=2)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 200889899-Chloro-7-dodecyl-1,2,3,4-tetrahydroacridine

Product 1

HCID 200890099-Benzylamino-7-dodecyl-1,2,3,4-tetrahydroacridine hydrochloride

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Procedure

9-Chloro-7-dodecyl-1,2,3,4-tetrahydroacridine (2.85 g) was heated at 150° in 60 mL of phenol containing 2.46 g of benzylamine. After 3 hours the reaction mixture was distributed between Et2O and 10% NaOH aqueous solution. The organic phase was washed once more with 10% NaOH, once with H2O, and then treated with 5% HCl. The insoluble hydrochloride was filtered off and recrystallized from isopropanol to give 2.15 g of analytically pure product, mp 194°-195°.

Workup

  1. washThe organic phase was washed once more with 10% NaOH, once with H2O
  2. additiontreated with 5% HCl
  3. filtrationThe insoluble hydrochloride was filtered off
  4. customrecrystallized from isopropanol
  5. customto give 2.15 g of analytically pure product, mp 194°-195°

Sources & evidence

ORD record
ord-4737f658f8a6456386cbf71bd19da64b
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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