N,N-Dimethyl-3-(4-nitrophenoxy)-1-propanamine synthesis
- Product Name:N,N-Dimethyl-3-(4-nitrophenoxy)-1-propanamine
- CAS Number:91430-80-7
- Molecular formula:C11H16N2O3
- Molecular Weight:224.26
3179-63-3
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Yield:91430-80-7 92%
Reaction Conditions:
with sodium hydride in N,N-dimethyl-formamide at 20 - 35; for 4 h;
Steps:
1.A
EXAMPLE 1; [4-(3-Dimethylamino-propoxy)-phenyl]-(3-indan-5-yl-3H-[1,2,3]triazolo- [4,5-dipyrimidin-5-yl)-amine (Cpd 1); To a suspension of NaH (60% in oil, 3.87 g, 96.8 mmol) in DMF (80 ml_) was added a solution of 3-dimethylamino-1-propanol (5 g, 48.46 mmol) in DMF (10 mL). The temperature was maintained below 35 C during the addition, and then cooled to 25 C. A solution of 1 -fluoro-4-nitrobenzene (5.14 mL, 48.45 mmol) in DMF (10 mL) was added slowly to the reaction mixture. The mixture was stirred at room temperature for 4 h. The reaction mixture was carefully poured into ice-water and extracted with ether (2 x 300 mL). The combined organic layers were dried over MgSO4 and concentrated to give desired product 1c (9.98g, 92%). Compound 1c was used in the next reaction without further purification. MS (ES+) m/z 225.0 (M+H+); 1H NMR (CDCI3, 300 MHz): δ 2.01 (m, 2H), 2.27 (S, 6H), 2.47 (t, 2H), 4.15 (t, 2H), 6.98 (d, 2H), 8.20 (d, 2H).
References:
WO2006/76442,2006,A2 Location in patent:Page/Page column 40
