3-(4-Methylpiperazin-1-yl)benzaldehyde synthesis
- Product Name:3-(4-Methylpiperazin-1-yl)benzaldehyde
- CAS Number:628325-62-2
- Molecular formula:C12H16N2O
- Molecular Weight:204.27
109-01-3
678 suppliers
$5.00/5 g
75148-49-1
117 suppliers
$19.69/5g
628325-62-2
40 suppliers
$60.00/100mg
Yield: 42%
Reaction Conditions:
Stage #1:1-methyl-piperazine;3-bromobenzaldehyde diethylacetal with tris-(dibenzylideneacetone)dipalladium(0);2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;sodium t-butanolate in toluene at 100; for 18 h;Inert atmosphere;
Stage #2: with hydrogenchloride;water in toluene for 2.5 h;
Steps:
1 3-(4-Methylpiperazin-1-yl)benzaldehyde
To a solution of 3-bromobenzylaldehyde diethyl acetal (0.518 g, 2.0 mmol) and15 anhydrous toluene (4 ml) was added 1-methylpiperazine (0.240 g, 2.4 mmol) followedby Pd2(dba)3 (0.018 g, 0.02 mmol), racemic BINAP (0.037 g, 0.06 mmol) and Na01Bu(0.326 g, 3.4 mmol). The reaction mixture was placed into an oil bath preheated to 100°C and stirred at this temperature for 18 h under argon, then allowed to cool to roomtemperature. Aqueous HCI (1M; 10 ml) was added, the mixture was vigorously stirred20 for 2.5 h, then the pH adjusted to 13 with 6M aqueous NaOH and extracted with ethylacetate (3 x 30 ml). The combined organics were dried (Na2S04), concentrated in vacuoand the residue was absorbed on silica gel and placed on a 10 g isolute column. Elutionwith ethyl acetate I dichloromethane (v/v; 4:1) and then a gradient of methanol (3 to 7%)in ethyl acetate afforded the title compound as a yellow oil (0.170 g, 42%). 1 H-NMR (50025 MHz, DMSO-d6) 2.22 (s, 3H, N-Me), 2.46 (t, J = 5.0 Hz, 4H, piperazine C-H), 3.21 (t, J =5.1 Hz, 4H, piperazine C-H), 7.28 (m, 2H, PhH), 7.41 (m, 2H, PhH), 9.94 (s, 1 H, CHO);[00122] LC- MS (ESI, m/z): Rt = 0.86 min- 205 (M+Ht.
References:
CANCER RESEARCH TECHNOLOGY LIMITED;BLAGG, Julian;BAVETSIAS, Vassilios;MOORE, Andrew S.;LINARDOPOULOS, Spyridon WO2013/190320, 2013, A1 Location in patent:Paragraph 00121
3132-99-8
502 suppliers
$5.00/10g
628325-62-2
40 suppliers
$60.00/100mg
67437-93-8
10 suppliers
inquiry
628325-62-2
40 suppliers
$60.00/100mg
109-01-3
678 suppliers
$5.00/5 g
17789-14-9
147 suppliers
$6.00/1g
628325-62-2
40 suppliers
$60.00/100mg
17789-14-9
147 suppliers
$6.00/1g
628325-62-2
40 suppliers
$60.00/100mg