Tacrine → HCID 15728810, compound

HRID 2050499Notes

Reaction equation

HRID 2050499 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.[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[F:22][C:23]([F:32])([F:33])[C:24]1[CH:25]=[CH:26][C:27]([CH:28]=[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:30][CH:31]=1

Participants

5

Reactant 3

HCID 1935TacrineHCID 8083MorpholineHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 15728810HCID 15728810, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2,3,4-Tetrahydro-9-acridinamine (4.00 g) was refluxed for twenty-four (24) hours in 400 ml of toluene that contained morpholine (3.50 g) and 4-trifluoromethylbenzaldehyde (4.35 g). At this time, an additional 2.0 g of aldehyde was added and reflux was continued for another sixteen (16) hours. At the end of this time the reaction mixture was concentrated and the residue was purified by flash chromatography (CH2Cl2, then 20% EtOAc/CH2Cl2). Fractions containing the product were concentrated and recrystallized from benzene/pentane to give 3.46 g of analytically pure product, m.p. 203°-205° C.

Workup

  1. temperaturereflux
  2. concentrationAt the end of this time the reaction mixture was concentrated
  3. customthe residue was purified by flash chromatography (CH2Cl2
  4. additionFractions containing the product
  5. concentrationwere concentrated
  6. customrecrystallized from benzene/pentane
  7. customto give 3.46 g of analytically pure product, m.p. 203°-205° C.

Sources & evidence

ORD record
ord-52d31232dc794795bcd6e35b1ab83bab
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

Loading…