Benzylamine → HCID 20089023, compound

HRID 274873Notes

Reaction equation

HRID 274873 reaction equation
Cl.[Cl:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[C:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:5]=2.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].[Na+]>C1(O)C=CC=CC=1>[ClH:2].[CH2:27]([NH:34][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[C:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:5]=2)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 20088983HCID 20088983, compound

Product 1

HCID 20089023HCID 20089023, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Procedure

9-Chloro-7-decyl-1,2,3,4-tetrahydroacridine hydrochloride (5.0 g) was dissolved in 50 ml of phenol and heated at 150° C. with 3.50 g of benzylamine. After 2 hours at this temperature the reaction mixture was poured into 10% NaOH and extracted with Et2O. The organic phase was separated, washed with water and treated with 5% HCl. The insoluble hydrochloride was filtered off and recrystallized from MeOH/Et2O to give 2.59 g of product, m.p. 215° C.

Workup

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

Sources & evidence

ORD record
ord-2906f9efaef3499a9c22b8b0cf25730b
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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