Phenethylamine → HCID 14536417, compound

HRID 1607879Notes

Reaction equation

HRID 1607879 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14](O)[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:17]1([CH2:23][CH2:24][NH2:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[C:17]1([CH2:23][CH2:24][NH:25][CH:14]2[C:15]3[C:10](=[N:9][C:8]4[C:3]([C:2]=3[NH2:1])=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:11][CH2:12][CH2:13]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 3655VelnacrineHCID 6101p-Toluenesulfonic acidHCID 14798Sodium Hydroxide

Product 1

HCID 14536417HCID 14536417, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 9-amino-1,2,3,4-tetrahydroacridin-1-ol (8.82 g), phenylethylamine (15.6 ml) and p-toluensulfonic acid (8.7 g) in 250 ml of toluene was refluxed with removal of water for twenty hours. The mixture was then treated with a dilute NaOH solution, and extracted with ethyl acetate (3x). The combined organics were washed with water and dried (saturated NaCl solution, MgSO4).

Workup

  1. extractionextracted with ethyl acetate (3x)
  2. washThe combined organics were washed with water
  3. dry with materialdried (saturated NaCl solution, MgSO4)

Sources & evidence

ORD record
ord-c943177a9da141168fc6df06c4ff2337
Source dataset
uspto-grants-1989_09
Patent number
US04868177

Reaction notes

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