1-Naphthalenemethanamine → HCID 57495446, compound

To a solution of suberic acid monomethyl ester 6c (376 mg, 2.0 mmol) in anhydrous tetrahydrofuran (5 ml) under argon atmosphere triethylamine (0.36 ml, 2.6 mmol) was added and the resulting solution was cooled in ice bath. To the mixture iso-butylchloroformate (0.3 ml, 2.3 mmol) was added and the reaction was stirred for 20 min, then a solution of 1-naphthylmethylamine 1/89 (314 mg, 2 mmol) in tetrahydrofuran (1.5 ml) was added. The mixture was stirred at ice bath temperature for 15 min and for 1 h at room temperature, diluted with brine (50 ml) and extracted with ethyl acetate (3×25 ml). The organic phase was washed with brine, 5% NaHCO3, brine, saturated KH2PO4, and brine. The organic layer was dried (Na2SO4) and the solvent was evaporated. The residue was purified on silica gel (20 g) with chloroform-ethyl acetate as eluent to give the title compound 7/89, yield 85.4%. 1H NMR (CDCl3, HMDSO) δ: 1.12-1.81(m, 8H); 2.16(t, J=8.0 Hz, 2H); 2.25(t, J=8.0 Hz, 2H); 3.63(s, 3H); 4.87(d, J=6.0 Hz, 2H); 5.61(br s, 1H); 7.32-7.63(m, 4H); 7.67-8.09(m, 3H).

1. temperaturethe resulting solution was cooled in ice bath
2. stirringThe mixture was stirred at ice bath temperature for 15 min
3. waitfor 1 h at room temperature
4. extractionextracted with ethyl acetate (3×25 ml)
5. washThe organic phase was washed with brine, 5% NaHCO3, brine, saturated KH2PO4, and brine
6. dry with materialThe organic layer was dried (Na2SO4)
7. customthe solvent was evaporated
8. customThe residue was purified on silica gel (20 g) with chloroform-ethyl acetate as eluent

ORD record

ord-b858fc3241314d53bde9be701e1b8bd7

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569724B2