1''-METHYL-5-METHOXYSPIRO[INDOLE-3,4''-PIPERIDINE]2(1H)ONE synthesis
- Product Name:1''-METHYL-5-METHOXYSPIRO[INDOLE-3,4''-PIPERIDINE]2(1H)ONE
- CAS Number:742067-27-2
- Molecular formula:C14H18N2O2
- Molecular Weight:246.3
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Yield:-
Reaction Conditions:
Stage #1:5-methoxyindolin-2-one with sodium hexamethyldisilazane in tetrahydrofuran at -78; for 0.5 h;
Stage #2:mechlorethamine hydrochloride at 20; for 13.5 h;
Steps:
4.4-0.L intermediate L
To a solution of 5-methoxy-1,3-dihydro-indol-2-one (1.06 g, 6.49 mmol) in THF (13 ml), a solution of NaHMDS (1 M THF solution) (32.5 ml, 32.5 mmol) is added at -78 C. After stirring for 30 min at-78 C, methyl-bis-(2-chloro-ethyl)-amine hydrochloride (1.37 g, 7.14 mol) is added and the reaction mixture is stirred for 13.5 h at room temperature, quenched with sat. NH4Cl aq. and ice-water and extracted with ethyl acetate. The organic extracts are washed with brine, dried over sodium sulphate and evaporated down. Ethyl ether is added to the residue to give the powder, which is filtrated. Rf=0.10 (CH2CI2:MeOH = 30:1) 1H-NMR (400 MHz, DMSO-d6) δ: 1.66-1.78 (m, 4H), 2.28 (s, 3H), 2.44-2.47 (m, 2H), 2.71-2.77 (m, 2H), 3.70 (s, 3H), 6.74 (s, 2H), 7.01 (s, 1H), 10.15 (brs, 1H)
References:
NOVARTIS AG;NOVARTIS PHARMA GMBH WO2004/76455, 2004, A1 Location in patent:Page 41
