ChemicalBook CAS DataBase List AKOS B023083

AKOS B023083 synthesis

6synthesis methods

Product Name:AKOS B023083
CAS Number:161119-99-9
Molecular formula:C8H13NO
Molecular Weight:139.19

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161119-99-9
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Yield:-

Reaction Conditions:

with sodium tetrahydroborate in methanol;dichloromethane at 5 - 20; for 24 h;

Steps:

Synthesis of N-furfuryl-N-isopropylamine

Isopropylamine (0.4 ml, 4 mmol) and furfuraldehyde (0.4 ml, 5.1 mmol) were dissolved inmethanol (10 ml) and the solution was stirred for 2 h at room temperature. The solvent wasremoved by evaporation. The resulting yellow oil was dissolved in methanol-dichloromethanesolvent mixture (1:1, 20 ml) and sodium borohydride (0.5 g, 13.8 mmol) was added slowly at5C. The mixture was stirred at room temperature for 24 h. After evaporation of the solvent, theresulting viscous liquid was washed with water and dichloromethane was added in order to extractthe product. Evaporation of the organic layer gave N-furfuryl-N-isopropylamine as yellow oil.1H NMR (400 MHz, CDCl3, ppm): δ = 1.07 (d, 6H, J = 6.0 Hz, methyl protons), 2.06 (b, 1H,NH), 2.78-2.84 (m, 1H, methine proton), 4.82 [s, 2H, NCH2(furfuryl)], 6.16 [b, 1H, H-4 (furyl)],6.30 [dd, 1H, J = 1.2 Hz, H-3 (furyl)], 7.34 [d, 1H, J = 0.8 Hz, H-5 (furyl)]. 13CNMR(100 MHz,CDCl3, ppm): δ = 22.7 (methyl carbons), 43.8 (methine carbons), 47.6 [NCH2(furfuryl)], 106.6,110.1, 141.7, 154.1(furyl carbons).

References:

Rani, Palanisamy Jamuna;Thirumaran, Subbiah;Ciattini, Samuele [Journal of Sulfur Chemistry,2014,vol. 35,# 1,p. 106 - 116]

617-89-0 Synthesis