Benzylamine → HCID 20089005, compound

HRID 274870Notes

Reaction equation

HRID 274870 reaction equation
Cl[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][C:6]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5][CH:4]=2.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>C1(O)C=CC=CC=1>[CH2:20]([NH:27][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][C:6]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5][CH:4]=2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 20089024HCID 20089024, compound

Product 1

HCID 20089005HCID 20089005, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Procedure

9-Chloro-6-(1,1-dimethylethyl)-1,2,3,4-tetrahydroacridine (3.0 g) was dissolved in 60 ml of phenol and heated at 150° C. with 3.54 g of benzylamine. After 2 hours the reaction mixture was poured into 10% NaOH and extracted with Et2O. The organic phase was separated, washed with H2O, and then treated with 5% HCl. The insoluble hydrochloride was filtered off and recrystallized from isopropanol/ether and then from methanol/ether to give 2.09 g of product, m.p. 247° (d).

Workup

  1. extractionextracted with Et2O
  2. customThe organic phase was separated
  3. washwashed with H2O
  4. additiontreated with 5% HCl
  5. filtrationThe insoluble hydrochloride was filtered off
  6. customrecrystallized from isopropanol/ether

Sources & evidence

ORD record
ord-866be33b520149aa9e096b7a35fc57f1
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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