Dimethylamine → N,N-Dimethylphenylethylamine

To a stirring solution of phenylacetaldehyde (5 mM, 0.6 mL) and dimethylamine (5 mM, 3 mL of 2M in MeOH) in MeOH (1 mL), was added NaCNBH3 (5 mM, 360 mg) in a round-bottomed flask. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and H2O was added to the residue before extraction with CH2Cl2. The combined extracts were dried over MgSO4, the solid was filtered off, and the solvent was evaporated under reduced pressure to give a yellow oil. The crude products were purified by column chromatography (silica gel, EtAc:n-hexane, 4:6) to afford pure product in quantitative yield, 0.52 g, 87%, yellow oil. TLC (EtAc:n-hex, 4:6 v/v): RF=0.2. 1H NMR, δ: 7.40-7.20 (m, 5H), 3.20 (m, 4H), 2.20 (S, 6H). 13C NMR, δ: 141.5, 129.1, 128.6, 125.8, 60.9, 45.6, 32.2. Anal. calcd for C10H13N: C, 80.48; H, 10.13; N, 9.39%. Found; C, 90.60; H, 10.20; N, 9.40%.

1. customThe solvent was evaporated
2. additionH2O was added to the residue before extraction with CH2Cl2
3. dry with materialThe combined extracts were dried over MgSO4
4. filtrationthe solid was filtered off
5. customthe solvent was evaporated under reduced pressure
6. customto give a yellow oil
7. customThe crude products were purified by column chromatography (silica gel, EtAc:n-hexane, 4:6)
8. customto afford pure product in quantitative yield, 0.52 g, 87%, yellow oil

ORD record

ord-c981001fea5b42e88ac8a127eab38685

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349898B2