4-Aminoindane

Intermediate 8: 4-aminoindane In a 500 mL Parr shaker vessel, 4-nitroindane (10 g, 61 mmol) was dissolved in 50 mL ethanol. A slurry of 10percent Pd/C (1 g) in ethanol was added. The mixture was then placed on a Parr shaker under a hydrogen atmosphere (50 psi) for 1 hour, at which point t.l.c. (20percent ethyl acetate in hexanes) showed that all the starting material had disappeared. To work up the reaction, the mixture was filtered twice through Celite, washing with a large amount of ethanol, and once through filter paper. The ethanol was evaporated under reduced pressure, and the crude product purified by flash chromatography over silica gel (10percent ethyl acetate in hexanes) to give 8 as a viscous, faintly colored oil (7.04 g, 86percent yield): To a stirring solution of acetic anhydride (14 mL, 278 mmol) in EtOH (150m1) was addedthe solution of Example 19: Synthesis of Compound XIII-30; Step 1 : Synthesis of N-(2-3-dihydro-lH-inden-4-yl)acetamide (2); To a solution of 4-amino indane (1, 5 g, 37.5 mmol) in ethanol ( 1 1 1 mL) was taken, acetic anhydride (7.3 mL, 74.8 mmol) in ethanol (20 mL) was added drop wise at 0 C and stirred at RT for 1 h. Reaction was monitored by TLC. After completion of the reaction, ethanol was evaporated under reduced pressure, triturated with diethyl ether to afford N-(2, 3-dihydro-l H-inden-4-yl)acetamide as off-white solid (2, 6.5 g, 98.9%) NMR (400 MHz, CDCI3): delta 7.80-7.70 (d, 1 H), 7.20-7. 10 (t, 1H), 7.10-7.00 (d, 1 H), 3.00-2.90 (t, 2H), 2.90-2.70 (t, 2H), 2.21 (s, 3H), 2.20-2.10 (t, 2H).A solution of A mixture of To a solution of (1242) [00410] Into a 250-mL round-bottom flask was added 2, 3-dihydro-l -inden-4-amine (5.00 g, 37.5 mmol) and ethanol (100 mL). Acetic anhydride (7.67 g, 7.10 mL, 75, 1 mmol) was added and the resulting solution was stirred for 1 h at RT. The reaction mixture was concentrated in vacuo and then diluted with ether (20 mL). The solid product was collected by filtration and dried in vacuo to afford A -(2, 3-dihydro-lH-inden-4-yl)acetamide as an off-white solid (6.0 g, 91%). LCMS (ESI, m/z): i 76To a solution of 2, 3-dihydro-lH-inden-4-amine (3.4 g, 26 mmol) in ethanol (45 mL) was added a solution of acetic anhydride (4.9 mL, 52 mmol) in ethanol (15 mL) dropwise at 0 C. The resulting mixture was gradually warmed up to RT and stirred for 15 h. Solvent was removed under reduced pressure and the residue was triturated with diethyl ether to afford titled compound as off white solid (3 g, 66%). LCMS [M+H]+= 176.3.A solution of 2, 3-dihydro-1 H-inden-4-amine, 1 (500 mg, 3.75 mmol) in EtOH (5 mL) was cooled to 0 C and treated dropwise with acetic anhydride (0.95 g, 9.37 mmol) under nitrogen atmosphere. The resulting reaction mixture was warmed to RT and stirred for 3h. Upon completion of reaction, (TLC, 30% ethyl acetate-hexanes, Rf, 0.2), the reaction mixture was concentrated in vacuo. The residue obtained was diluted with diethyl ether, filtered and dried in vacuo to give A/-(2, 3-dihydro-1 /-/-inden-4-yl)acetamide (0.3 g, 45%) as a white solid.1H NMR (400 MHz, DMSO-afe): delta = 9.29 (s, 1 H), 7.41 (d, J = 8.0 Hz, 1 H), 7.08 (t, J = 7.6 Hz, 1 H), 6.99 (d, J = 6.8 Hz, 1 H), 2.87 (t, J = 7.2 Hz, 2H), 2.80 (t, J = 7.2 Hz, 2H), 2.04 (s, 3H), 1 .99-1 .95 (m, 2H). LCMS (m/z): 176.40 [M+H]+

Molecular Weight:133.19
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:133.089149355
Monoisotopic Mass:133.089149355
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes