(4-AMINOMETHYL-PHENYL)-METHANOL

Off-White Solid

(4-Aminomethyl-phenyl)-methanol hydrochloride salt 4-Hydroxymethyl-benzonitrile (2.0 g, 15 mol) was reduced using Raney nickel (0. 5g) and hydrogen (50 psi) in MeOH: NH3 (100ml) for 20 hours. The reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to afford (4-aminomethyl-phenyl)-methanol hydrochloride salt (2.01 g, 98percent) as a white solid of sufficient purity for use without further purification: MS (APCI+) : m/z 138.3 (M+H); H-NMR (DMSO-d6) 8 7.20 (s, 4 H), 5.04 (s, 2 H), 4.42 (s, 2 H), 3.83 (s, 1 H), 2.45 (s, 2 H).Example 99 To a stirred suspension of LiAlHU (285 mg, 7.52 mmol) in diethylether (10 mL)at 0° C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t, the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CHTo a suspension of lithium aluminium hydride in tetrahydrofuran (400 mL) stirred in air at 0 °C was added a solution of methyl 4-cyanobenzoate (10 g, 62.1 mmol) in tetrahydrofuran (400 mL) dropwise over 15 minutes. The reaction mixture was stirred at 50 °C for 15 hours and then cooled to 0°C and quenched by the slow addition of water (7 mL), 15percent NaOH (7 mL), and water (21 mL). The resulting precipitate was stirred for an additional 30 minutes and filtered. The filtrated was concentrated in vacuo to give (4- (aminomethyl)phenyl)methanol (6.8 g, 80percent yield) as a light yellow oil. LCMS m/z = 138.0 [M+H]1.6 l-(Aminomethyl)-4-(hydroxymethyl)benzene, 6.6Azide 5 (1.96 g, 12.0 mmol) and PPhTo a cooled suspension of lithium aluminu 3 mmol) in tetrahydrofuran (50 mL) at 0 °C was added a solution of 4-formylbenzonitrile (5 g, 38.1 mmol) in tetrahydrofuran (50 mL). The resultant mixture was stirred at room temperature overnight then recooled to 0 °C and treated with a solution of aqueous sodium hydroxide solution (5 N, 32.1 mL). The resultant mixture was then filtrated and the filtrate concentrated in vacuo to provide (4-(aminomethyl)phenyl)methanol (4.5 g, 73 percent) as a white solid. LCMS m/z = 138.1 [M+H]

Molecular Weight:137.18
XLogP3:0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:137.084063974
Monoisotopic Mass:137.084063974
Topological Polar Surface Area:46.2
Heavy Atom Count:10
Complexity:87.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes