1-[4-(1,3-BENZOXAZOL-2-YL)PHENYL]METHANAMINE synthesis
- Product Name:1-[4-(1,3-BENZOXAZOL-2-YL)PHENYL]METHANAMINE
- CAS Number:760111-76-0
- Molecular formula:C14H12N2O
- Molecular Weight:224.26
Yield:-
Reaction Conditions:
Stage #1: p-aminomethylbenzoic acid;2-amino-phenolwith PPA at 170; for 1.5 h;
Stage #2: with water;potassium carbonate at 20;
Steps:
1
Synthesis of compound of formula Ia4-Aminomethyl-benzoic acid (1.0 g, 6.8 mmol) and 2-aminophenol (0.69 g, 7.4mmol) were mixed together with polyphosphoric acid (10 g) and heated to 17O0C underN2 atmosphere for 1.5 hours. The reaction mixture was cooled to room temperature andpoured into 10 % K2CO3 solution. The precipitate was filtered under reduced pressure.The precipitate was recrystallized from acetone-water followed by treatment withactivated charcoal in THF-water to obtain 4-benzooxazol-2-yl-benzylamine (Ia).R/ 0.65 (EtOAc/hexane 1 :2); 1H NMR (CDCl3): δ 8.20 (d, 2 H), 7.76 (dd, 1 H),7.66 (dd, 1 H), 7.55 (d, 2 H), 7.41 (m, 2 H), 3.90 (s, 2 H); MS (MALDI-TOF) m/z 225.33(M+H)+ calcd for Ci4H13N2Oi 225.09.
References:
WO2008/51017,2008,A1 Location in patent:Page/Page column 37
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