4-(N-BOC-AMINOMETHYL)ANILINE

White solid

To a mixture of 28 (590mg, 2.33mmol) in methanol (20.6mL) was added Pd/C (62mg; 10percent pp). The reaction mixture was hydrogenated under 35 PSI pressure at room temperature and for 2h. The reaction mixture was filtered and evaporated. Residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 as eluent) to furnish 29 (520mg; 100percent) as an oil. Step 2. Under nitrogen, Palladium carbon (200 mg) was addedTo a solution of tert-butyl (4-nitrobenzyl) carbamate (2.4 g, 9.5 mmol) in ethanol (40 ml).The reaction solution was allowed to react at room temperature for 3 hours in a hydrogen atmosphere (1 atm).The catalyst was removed by filtration, The organic phase was evaporated to dryness to give tert-butyl (4-aminobenzyl) carbamate (1.94 g, 91percent yield).(4-Nitro-benzyl) -carbamic acid tert-butyl ester (6.34g, 25. 1mmol), iron powder (6. 5g, 116MMOL), ammonium formate (13. 0g, 206MMOL), H20 (75MLS), and toluene (75MLS) were combined and heated to reflux. After 3hrs the reaction mixture was allowed to cool and filtered through Celite with thorough washing with EtOAc. The filtrate was transferred to a separatory funnel and the phases separated. The organic phase was further washed with H20 (LX), sat'd NaCl (LX), dried (NA2S04), and concentrated in vacuo to give (4-amino-benzyl) -carbamic acid tert- butyl ester (5.02g, 90percent yield).(4-Nitro-benzyl) -carbamic acid tert-butyl ester (6.34g, 25. 1mmol), iron powder (6. 5g, 116MMOL), ammonium formate (13. 0g, 206MMOL), H20 (75MLS), and toluene (75MLS) were combined and heated to reflux. After 3hrs the reaction mixture was allowed to cool and filtered through Celite with thorough washing with EtOAc. The filtrate was transferred to a separatory funnel and the phases separated. The organic phase was further washed with H20 (LX), sat'd NaCl (LX), dried (NA2S04), and concentrated in vacuo to give (4-amino-benzyl) -carbamic acid tert- butyl ester (5.02g, 90percent yield).Step III: To a solution of tert-butyl4-nitrobenzylcarbamate (compound 18C, 400 mg, 1.59 mmol) and Pd/C (50 mg) in MeOH (15 mL) was stirred at 25 °C under H2 atmosphere for20 0.5 hr. The reaction mixture was filtered and the filtrate was concentrated to give tert-butyl4-aminobenzylcarbamate (compound 18D, 300 mg) as a red solid, which was used in the next stepdirectly. MS: calc'd 223 (M+Ht, measured 223 (M+Ht.A mixture of 7 g (57.2 mmol) 4-aminobenzylamine (commercially available), 13.7 g (63 mmol) BocExample 82 tert-butyl N-[(4-aminophenyl)methyl]carbamate4-Amino-benzylamin (2 ml; 17, 6 mmol) wurde in 1, 4-Dioxan (10 ml) gelost. Unter Ruhren wurde eine wassrige 2 N NaOH-Losung (17, 6 ml; 35, 2 mmol) zugegeben. Eine Losung von Di-tert-butyl-pyrocarbonat (3, 08 g; 14, 1 mmol) in 1, 4-Dioxan (30 ml) wurde tropfenweise uber 30 min zugegeben und das Reaktionsgemisch uber Nacht bei Raumtemperatur geruhrt. Die Losung wurde im Vakuum auf etwa 10 ml konzentriert und zweimal mit Ethylacetat (30 ml) extrahiert. Die vereinigten organischen Phasen wurden mit wassrigem 5percent KHSO4 (10 ml), wassrigem 5percent NaHCO3, Wasser und Salzlosung gewaschen, uber wasserfreiem Na2SO4 getrocknet und im Vakuum eingedampft, wobei das Produkt als hellgelbe Festsubstanz erhalten wurde.Ausbeute:2, 38 g (76 percent); HPLC: tR 5, 6 min; MS 223 (M + H) +, berechnet 222 (M).

An aniline derivative used in the preparation of various organic synthase inhibitors and other bio-active compounds.

Molecular Weight:222.28
XLogP3:1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:222.136827821
Monoisotopic Mass:222.136827821
Topological Polar Surface Area:64.4
Heavy Atom Count:16
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes