Tacrine → HCID 15728809, compound

HRID 2050498Notes

Reaction equation

HRID 2050498 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.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][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:26][CH:25]=1

Participants

5

Reactant 3

HCID 1935TacrineHCID 8083MorpholineHCID 312444-Methoxybenzaldehyde

Product 1

HCID 15728809HCID 15728809, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2,3,4-Tetrahydro-9-acridinamine (4.0 g) was refluxed overnight in 400 ml of toluene containing 3.5 g of morpholine and 3.4 g of 4-methoxybenzaldehyde. At the end of this time, an additional 1.7 g of aldehyde was added and heating was continued for six (6) more hours. The reaction mixture was then concentrated and purified by flash chromatography (CH2Cl2, then 10% EtOAc/CH2Cl2). Fractions containing the product were concentrated and recrystallized from benzene/pentane to give 3.37 g of analytically pure material, m.p. 160°-162° C.

Workup

  1. temperatureheating
  2. concentrationThe reaction mixture was then concentrated
  3. custompurified by flash chromatography (CH2Cl2
  4. additionFractions containing the product
  5. concentrationwere concentrated
  6. customrecrystallized from benzene/pentane
  7. customto give 3.37 g of analytically pure material, m.p. 160°-162° C.

Sources & evidence

ORD record
ord-322f4cc112b341d2979dbaa476c5a230
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

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