Tacrine → HCID 15728804, compound

HRID 2050494Notes

Reaction equation

HRID 2050494 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.[C:22]1([CH3:30])[C:23]([CH:28]=O)=[CH:24][CH:25]=[CH:26][CH:27]=1>C1(C)C=CC=CC=1>[CH3:30][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH:28]=[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 8083MorpholineHCID 107222-Methylbenzaldehyde

Product 1

HCID 15728804HCID 15728804, 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 o-tolualdehyde (3.0 g) were successively added. The reaction mixture was refluxed overnight and then an additional 1.5 g of aldehyde was added. Reflux was continued for an additional six (6) hours and then the reaction mixture was concentrated and purified by flash chromatography (CH2Cl2, then 20% EtOAc/CH2Cl2). Fractions containing the pure product were concentrated and recrystallized from benzene/pentane to give 3.32 g of analytically pure product, m.p. 160°-162° 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 pure product
  7. concentrationwere concentrated
  8. customrecrystallized from benzene/pentane
  9. customto give 3.32 g of analytically pure product, m.p. 160°-162° C.

Sources & evidence

ORD record
ord-563156f592ed4085a718a6676029c8fb
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

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