Benzaldehyde → HCID 9860677, compound

HRID 2050493Notes

Reaction equation

HRID 2050493 reaction equation
[CH2:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.N1CCOCC1.O.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C1CCCCC1>[C:24]1([CH:23]=[N:15][C:13]2[C:12]3[C:7]([N:6]=[C:5]4[C:14]=2[CH2:1][CH2:2][CH2:3][CH2:4]4)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 1935TacrineHCID 8083Morpholine

Product 1

HCID 9860677HCID 9860677, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8078CyclohexaneSolvent

Procedure

1,2,3,4-Tetrahydro-9-acridinamine (4.0 g) was dissolved in 400 ml of warm toluene and then morpholine (3.5 g) and benzaldehyde1 (2.65 g) were added and the reaction mixture was brought to reflux with a Dean-Stark water separator. After the solution was refluxed overnight an additional 2.65 g of benzaldehyde was added and reflux was continued an additional five (5) hours. At the end of this time the volatiles were removed under reduced pressure and the residue was purified by flash chromatography (EtOAc) to give 3.18 g of pure porduct after trituration with Et2O. Analytically pure material was obtained by recrystallization from cyclohexane, m.p. 168°-169° C.

Workup

  1. additionwas added
  2. temperaturereflux
  3. customAt the end of this time the volatiles were removed under reduced pressure
  4. customthe residue was purified by flash chromatography (EtOAc)
  5. customto give 3.18 g of pure porduct after trituration with Et2O

Sources & evidence

ORD record
ord-fc73f878da4a4579a5ce31123fd18257
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

Loading…