Benzaldehyde → (+)-Benzylphenethylamine

To a stirred solution of benzaldehyde (1.58 mL, 15.5 mmol) in 10 mL of absolute ethanol at room temperature under nitrogen was added (R)-α-methylbenzylamine (2.0 mL, 15.51 mmol, 99% ee.). The reaction mixture was stirred for 3 hours. The reaction solution was then dried over magnesium sulfate and diluted to a 60 mL volume with EtOH, Ethanol washed Raney nickel Ni (~1.5 g) was added and the resulting suspension was treated with 58 psi of hydrogen in a Parr Type Shaker. After 1 day, additional Raney nickel (~1 g) and 30 mL of ethanol were added and the hydrogenolysis continued for 3 days. The reaction mixture was filtered through Celite to remove the catalyst and concentrated to afford 3.11 g (95%) of N-benzyl (R)-α-methylbenzylamine as a pale yellow oil contaminated with ~5% of benzyl alcohol and (R)-α-methylbenzylamine; 1H NMR (DMSO-d6, 250 MHz)δ 7.1-7.5 (m, 10H, Ar), 3.68 (q, 1H, J=6.6 Hz), 3.48 (dd, 2H, J=13.6 Hz, J2=20.5 Hz), 1.26 (d, 3H, J=6.6 Hz, CH3); 13C NMR (DMSO-d6)δ 146.1, 141.0, 128.2, 128.0, 127.8, 126.5, 126.4, 56.7, 50.6, 24.5. This mixture was used directly in the next reaction.

1. dry with materialThe reaction solution was then dried over magnesium sulfate
2. additiondiluted to a 60 mL volume with EtOH, Ethanol
3. washwashed Raney nickel Ni (~1.5 g)
4. additionwas added
5. additionthe resulting suspension was treated with 58 psi of hydrogen in a Parr Type Shaker
6. waitAfter 1 day
7. additionadditional Raney nickel (~1 g) and 30 mL of ethanol were added
8. waitthe hydrogenolysis continued for 3 days
9. filtrationThe reaction mixture was filtered through Celite
10. customto remove the catalyst
11. concentrationconcentrated

ORD record

ord-dc873cf23e78440e9d1d1630fa5111ce

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06075041