1-(3,4-Dimethoxy-phenyl)-2-dimethylamino-ethanol synthesis
- Product Name:1-(3,4-Dimethoxy-phenyl)-2-dimethylamino-ethanol
- CAS Number:2970-95-8
- Molecular formula:C12H19NO3
- Molecular Weight:225.28
33061-24-4
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Yield:2970-95-8 80%
Reaction Conditions:
with sodium tetrahydroborate in methanol at 20; for 3.25 h;
Steps:
1-(3, 4-dimethoxy-phenyl)-2-dimethylamino-ethanol (10)
To a stirred solution of 1-(3,4-dimethoxy-phenyl)-2-dimethylamino-ethanone (9) (10 g, 0.0450 mol) in methanol (100 mL) at RT sodium boro hydride (8.7 g, 0.225 mol) portion wisely added over 15 min, maintained the reaction mixture at RT for 3 h, total reaction mass concentrated under reduced pressure and charged DM water (200 mL) and extracted with ethyl acetate (2 X 200 mL), organic layers dried over sodium sulfate and concentrated under reduced pressure, get oil (10) 8 g (80%); IR (KBr, Cm-1): 3270, 2779, 1684, 1266; Mass for C12H19NO3 [M+1] 225.0; 1H NMR (400 MHz, DMSO) (δ ppm): 2.27 (6H, s), 2.31 (1H, dd, J1 = 4.5 Hz, J2 = 4.49 Hz), 2.45 (1H, dd, J1 = 8.4 Hz, J2 = 8.33 Hz), 3.74 (6H, s), 4.58 (1H, t, J = 4.0 Hz), 4.59 (1H, s), 7.0 (1H, d, J = 8.3 Hz), 7.43 (1H, s), 7.71 (1H, dd, J1 = 1.46 Hz, J2 = 1.48 Hz); 13C NMR (100 MHz, DMSO) (δ ppm); 45.90, 53.46, 54.5, 67.9, 70.7, 110.2, 117.7, 118.4, 137.4, 148.0, 148.8.
References:
Pailla, Uma Reddy;Arava, Veera Reddy;Ravindhranath [Synthetic Communications,2014,vol. 44,# 15,p. 2232 - 2238] Location in patent:supporting information
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