Benzaldehyde → N-Benzyl-2-methylprop-2-en-1-amine

Add benzaldehyde (14.5 mL, 143 mmol) to a mixture of methallylamine (9.73 g, 137 mmol) and MgSO4 (15.0 g, 125 mmol) in THF (180 mL). Stir for 22 h, filter the mixture, and concentrate the filtrate. Dissolve the residue in EtOH (200 mL) and treat with NaBH4 (5.00 g, 132 mmol) in 3 portions. After 19 h, remove the solvent by rotary evaporation. Treat the residue with 1 M HCl (200 mL) then 5 M HCl (20 mL). Wash the solution with tert-butyl methyl ether (250 mL) and then treat with 5 M NaOH (50 mL) to make basic. Extract the mixture with CH2Cl2 (200 mL followed by 100 mL). Dry, filter and concentrate the organic solution to give the title compound (20.3 g, 92%) as a colorless liquid. 1H NMR (400 MHz, DMSO-d6): δ 7.2-7.4 (5H, m), 4.84 (1H, s), 4.79 (1H, s), 3.63 (2H, s), 3.03 (2H, s), 1.69 (3H, s).

1. filtrationfilter the mixture
2. concentrationconcentrate the filtrate
3. dissolutionDissolve the residue in EtOH (200 mL)
4. waitAfter 19 h
5. customremove the solvent
6. customby rotary evaporation
7. additionTreat the residue with 1 M HCl (200 mL)
8. washWash the solution with tert-butyl methyl ether (250 mL)
9. additiontreat with 5 M NaOH (50 mL)
10. extractionExtract the mixture with CH2Cl2 (200 mL followed by 100 mL)
11. customDry
12. filtrationfilter
13. concentrationconcentrate the organic solution

ORD record

ord-bc213b058d0e477881d92474aec3da87

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902356B2