Benzaldehyde → 2-(Benzylamino)-1-phenylethanol

To a solution of 2-amino-1-phenyl-ethanol (12.0 g, 87.48 mmol) in methanol (60 mL) was added benzaldehyde (9.3 g, 8.9 mL, 87.48 mmol) and the reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was then cooled to 0° C. and sodium borohydride (3.3 g, 87.48 mmol) was added. The reaction mixture was gradually allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated in vacuo, diluted with water, and filtered. The residue was rinsed with cold isopropanol (3×), then dried in vacuo to give 2-(benzylamino)-1-phenylethanol as white crystals (14.0 g, 70%). ESI-MS m/z calc. 227.1. Found 228.2 (M+1)+; Retention time:0.8 minutes (3 min run). 1H NMR (400 MHz, MeOD) δ 7.37-7.27 (m, 8H), 7.27-7.19 (m, 2H), 4.78 (dd, J=8.5, 4.5 Hz, 1H), 3.77 (q, J=13.0 Hz, 2H), 2.82-2.68 (m, 2H).

1. temperatureThe reaction mixture was then cooled to 0° C.
2. temperatureto warm to room temperature
3. stirringstirred overnight
4. concentrationThe reaction mixture was concentrated in vacuo
5. additiondiluted with water
6. filtrationfiltered
7. washThe residue was rinsed with cold isopropanol (3×)
8. customdried in vacuo

ORD record

ord-aed35b26e3794dc99f4e65ea0289b1f7

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828996B2