1H-Indole-3-propanamine

Light yellow powder

Step 2: To the solution of 3-(1H-indol-3-yl)propylamide (1.85 g, 9.83 mmol) in tetrahydrofuran (50 mL) is added lithium aluminum hydride (1.49 g, 39.31 mmol) at 0° C. The resulting mixture is warmed to room temperature and then refluxed for 2.5 hours. The mixture is then cooled to room temperature and quenched by slow addition of water (2 mL) followed by aqueous 15percent sodium hydroxide (2 mL) and water (2 mL). The mixture is allowed to stir overnight and filtered through celite. The filtrate obtained is evaporated and the residue is subjected to flash column chromatography (50percent dichloromethane: 40percent methanol: 10percent aqueous ammonia (40percent)) to afford 3-(1H-Indol-3-yl)propylamine (1.61 g, 94percent).Example 43-(1H-Indol-3-yl)-propylamine The title compound may be prepared from 3-(1H-indol-3-yl)propanoic acid according to Scheme B.3-(1H-Indol-3-yl)propylamine: [3-(1H-indol-3-yl)-propyl]-[2-(naphthalen-1-yloxy)-ethyl]-amine (13c) This compound was prepared in the manner described above for by replacing 2-(indan-4-yloxy)-ethylchloride with 2-(napthalen-1-yloxy)-ethylchloride (0.6 g, 2.8 mmol), and 3-(5-fluoro-1H-indol-3-y-)-propylamine with 3-(1H-indol-3-yl)-propylamine (1.35 g, 7.2 mmol) in 85percent yield (1.42 g) as a yellow solid: mp 119-120° C. The fumarate salt was prepared in ethanol: mp 203-205° C.; Elemental analysis for C23 H24 N2 O.0.5C4 H4 O4.0.25H2 O Calc'd: C, 73.78; H, 6.56; N, 6.88; Found: C, 73.74; H, 6.47; N, 6.89.Step 2: To the solution of 3-(1H-indol-3-yl)propylamide (1.85 g, 9.83 mmol) in tetrahydrofuran (50 mL) is added lithium aluminum hydride (1.49 g, 39.31 mmol) at 0° C. The resulting mixture is warmed to room temperature and then refluxed for 2.5 hours. The mixture is then cooled to room temperature and quenched by slow addition of water (2 mL) followed by aqueous 15percent sodium hydroxide (2 mL) and water (2 mL). The mixture is allowed to stir overnight and filtered through celite. The filtrate obtained is evaporated and the residue is subjected to flash column chromatography (50percent dichloromethane: 40percent methanol: 10percent aqueous ammonia (40percent)) to afford 3-(1H-Indol-3-yl)propylamine (1.61 g, 94percent).Example 43-(1H-Indol-3-yl)-propylamine The title compound may be prepared from 3-(1H-indol-3-yl)propanoic acid according to Scheme B.3-(1H-Indol-3-yl)propylamine: 1H NMR (300 MHz, DMSO-d6): delta 10.71 (s, 1H), 7.50 (d, J=7.5 Hz, 1H), 7.32 (td, J=8.4, 0.9 Hz, 1H), 7.08 (d, J=1.8 Hz, 1H), 7.04 (td, J=8.1, 1.2 Hz, 1H), 6.95 (td, J=7.2, 0.9 Hz, 1H), 2.69 (m, 2H), 2.59 (m, 2H), 1.71 (m, 2H); MS (ESI) m/z 175.0 (M+H+).General procedure: Reduction of amide or esters (Shirota et al., 2003). To a suspension of LiA1H4 (n g) in anhydrous THF was added drop-wise a solution of an amide (n g) in anhydrous THF. The mixture was refluxed for 24 h for amide reduction or 1 h for ester reduction, cooled to room temperature. The reaction was worked up by addition of water n mL, n mL of 15percent NaOH and 3n mL of water. The THF solution was filtered through celite and evaporated. To the residue was added iN of HC1 and the solution was extracted with EtOAc. To the aqueous layer was added saturated Na2CO3 until reaching pH = 10 and the solution was extracted with EtOAc. The organic layer was then dried over Na2SO4 and evaporated to give the product.3-(Indolin-1-yl)propan- 1-ol, (AN1400 free base). (Yushi et al., 2015) Compound 6afree base prepared from 3a by Procedure F, was isolated as a dark oil in 98percent yield.1H-Indole-3-propanamine, N-[1-(hydroxymethyl)-2-phenylethyl]-~-methyl-~-[[(tricyclo[3.3.1.13, 7 ]dec-2-ylcarbonyl)amino]methyl]-(indole center is RS, other center is S) The conversion of 19a to 20a was done in analogy to the conversion of 5a to 6a. After purification by chromatography on silica gel using CH2 Cl2 /MeOH 98:2 20a was isolated as a colorless amorphous solid (52percent), m.p. 85°-95° C. MS (70eV): m/z 527 (M+, 30), 335 (100).

Molecular Weight:174.24
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:174.115698455
Monoisotopic Mass:174.115698455
Topological Polar Surface Area:41.8
Heavy Atom Count:13
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes