Tacrine → HCID 15728806, compound

HRID 2050496Notes

Reaction equation

HRID 2050496 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.[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH:25]=O>C1(C)C=CC=CC=1>[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH:25]=[N:15][C:13]1[C:12]2[C:7]([N:6]=[C:5]3[C:14]=1[CH2:1][CH2:2][CH2:3][CH2:4]3)=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

5

Reactant 3

HCID 1935TacrineHCID 69962-ChlorobenzaldehydeHCID 8083Morpholine

Product 1

HCID 15728806HCID 15728806, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2,3,4-Tetrahydro-9-acridinamine (4.0 g) was suspended in 400 ml of toluene to which morpholine (3.5 g) and 2-chlorobenzaldehyde (3.5 g) were successively added. The reaction mixture was refluxed overnight and then an additional 1.7 g of aldehyde was added. Reflux was continued for an additional sixteen (16) hours and then the reaction mixture was concentrated and purified by flash chromatography (CH2Cl2, then 20% EtOAc/CH2Cl2). Fractions containing the product were concentrated and recrystallized from Et2O/pentane to give 2.10 g of analytically pure product, m.p. 165°-166° C.

Workup

  1. additionwere successively added
  2. temperatureThe reaction mixture was refluxed overnight
  3. temperatureReflux
  4. concentrationthe reaction mixture was concentrated
  5. custompurified by flash chromatography (CH2Cl2
  6. additionFractions containing the product
  7. concentrationwere concentrated
  8. customrecrystallized from Et2O/pentane
  9. customto give 2.10 g of analytically pure product, m.p. 165°-166° C.

Sources & evidence

ORD record
ord-fff7e6b014614cb28c6fc847ed562af9
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

Loading…