ChemicalBook CAS DataBase List 1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE

1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE synthesis

5synthesis methods

Product Name:1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE
CAS Number:321-64-2
Molecular formula:C13H14N2
Molecular Weight:198.26

108-94-1 Synthesis

108-94-1
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$12.00/50g

1885-29-6
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$5.00/1g

321-64-2
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$23.00/1g

Yield:321-64-2 98%

Reaction Conditions:

with zinc(II) chloride at 120; for 16 h;

Steps:

Preparation of tacrine moiety: Synthesis of 1,2,3,4-tetrahydroacridin-9-amine (1)
Zinc chloride (3.47g, 25.4mmol) was added to a mixture of 2-aminobenzonitrile (3g, 25.4mmol) and cyclohexanone (30.5mL, 294.6mmol). The reaction was kept at 120°C for 16h, then cooled to room temperature and the solvent was evaporated under reduced pressure. To the residue, 50mL of AcOEt were added and the resulting solid was collected after filtration. To the solid, 65mL of a 10% solution of NaOH in water was poured and kept under stirring overnight. After filtration, the cake was washed with H₂O (3×20mL), and then kept under stirring overnight with 30mL of MeOH. The solid was filtered and the solvent was evaporated under reduced pressure to give tacrine 1 as a yellow solid (4,95g, 98%): R_f=0.47 (CHCl₃/MeOH/NH₃ 7:3:0,1). mp=178-181°C. ¹H NMR (400MHz, CDCl₃): δ 7.89 (dd, J=8.5, 0.6Hz, 1H; H9), 7.68 (dd, J=8.4, 0.8Hz, 1H; H6), 7.55 (ddd, J=8.4, 6.8, 1.3Hz, 1H; H7), 7.35 (ddd, J=8.2, 6.8, 1.2Hz, 1H; H8), 4.65 (s, J=42.8Hz, 2H; NH₂), 3.01 (t, J=9.9Hz, 2H; H4), 2.60 (t, J=6.2Hz, 2H; H1), 1.99-1.84 (m, 4H; 2×H2, 2×H3). ¹³C NMR (101MHz, CD₃OD): δ 158.45, 150.72, 146.73, 129.84, 127.25, 124.51, 122.32, 118.20, 110.50, 33.86, 24.53, 23.76, 23.71.

References:

Cirillo, Davide;Dallanoce, Clelia;De Amici, Marco;Holzgrabe, Ulrike;Maspero, Marco;Messerer, Regina;Sotriffer, Christoph;Volpato, Daniela;Yuan Chen, Natalia [Bioorganic Chemistry,2020,vol. 96]

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