Tacrine → HCID 15728808, compound

HRID 2050497Notes

Reaction equation

HRID 2050497 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]=[C:27]([Cl:31])[C:24]=1[CH:25]=O>C1(C)C=CC=CC=1>[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[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 67372,6-DichlorobenzaldehydeHCID 8083Morpholine

Product 1

HCID 15728808HCID 15728808, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2,3,4-Tetrahydro-9-acridinamine (3.23 g) was suspended in 400 ml of toluene to which morpholine (2.8 g) and 2,6-dichlorobenzaldehyde (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 benzene/hexane to give 2.18 g of analytically pure product, m.p. 200°-202° 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 benzene/hexane
  9. customto give 2.18 g of analytically pure product, m.p. 200°-202° C.

Sources & evidence

ORD record
ord-7fcab57f07134680ad8940dc9b5e4eb8
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

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