Water → Carbamic acid, N-[2-(3-methoxyphenyl)ethyl]-, ethyl ester

To an ice-cold solution of 2-(3-methoxyphenyl)-1-ethanamine (5.00 g, 33.1 mmol) and Et3N (5.10 mL, 3.70 g, 36.6 mmol) in CH2Cl2 (100 mL) was added ethyl chloroformate (3.50 mL, 3.62 g, 33.4 mmol). The resulting solution was allowed to warm to RT and was stirred for 2 h. Water (100 mL) was added and the mixture was extracted with CH2Cl2 (3×50 mL), dried (MgSO4) and concentrated to yield ethyl 3-methoxyphenethylcarbamate (7.32 g, 99% yield) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.22 (t, J=7.8 Hz, 1H), 6.78 (d, J=8.0 Hz, 1H), 6.77 (d, J=8.0 Hz; 1H), 6.74 (s, 1H), 4.65 (brs, 1H), 4.11 (q, J=7.2 Hz, 2H), 3.80 (s, 3H), 3.44 (q, J=6.4 Hz, 2H), 2.79 (t, J=7.0 Hz, 2H), 1.23 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 224.2 (M+H+).

1. extractionthe mixture was extracted with CH2Cl2 (3×50 mL)
2. dry with materialdried (MgSO4)
3. concentrationconcentrated

ORD record

ord-3355603cebbd4f31a2ab288313765b38

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163756B2