1H-Inden-1-amine, 2,3-dihydro-N-2-propen-1-yl- synthesis
- Product Name:1H-Inden-1-amine, 2,3-dihydro-N-2-propen-1-yl-
- CAS Number:91639-43-9
- Molecular formula:C12H15N
- Molecular Weight:173.25
1875-50-9
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Yield:91639-43-9 84.5%
Reaction Conditions:
with pyridine;hydrogen in methanol at 20; for 6 h;High pressure;
Steps:
Synthesis of N-allyl-2,3-dihydro-1H-inden-1-amine or allyl impurity (4)
A solution of N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine (10) (10 g, 0.0584 mol, 1.0 eq), Lindlar catalyst (1.0 g, 10 % w/w) and catalytic amount of pyridine (0.456 g, 0.00584 mol, 0.1 eq) were taken in methanol (100 mL) and were hydrogenated by using hydrogen balloon pressure conditions for 6 h at ambient temperature. The reaction was monitored by using TLC, after completion of the reaction, the mixture was filtered through celite bed, MeOH was evaporated by high vacuum below 50 °C. The resultant crude was titrated by using EtOAc and n-hexane yielded 8.5 g (84.5 %) compound 4 as a brown colour oil. 1H NMR (400 MHz, DMSO); δ 7.32 (dd, 1H, Ar-H), 7.21-7.14 (m, 3H, Ar-H), 5.93-5.86 (m, 1H, =CH), 5.23-5.03 (m, 2H, =CH2), 4.10 (t, 1H, NH-CH), 3.60 (bs, 1H, NH) 3.29-3.22 (m, 2H, NHCH2), 2.89-2.69 (m, 2H, Ar-CH2), 2.49-2.27 (m, 2H, CH-CH2). Mass: m/z calcd. 173.12, found m/z 174.1 (M+1). HPLC purity (%): 91.70.
References:
Maruthi Raju;Moses Babu;Venkateswara Rao [Asian Journal of Chemistry,2017,vol. 29,# 6,p. 1357 - 1359]
83-33-0
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