HuagongsheHuagongshe Chemistry Print Report · For research reference only
(-)-Mandelic acid → (S)-N-Benzyl-1-(4-methoxyphenyl)propan-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (-)-Mandelic acid | HCID 11914 | — |
| Reactant | 4-Methoxy-alpha-methyl-N-(phenylmethyl)benzeneethanamine | HCID 3016422 | — |
| Product | (S)-N-Benzyl-1-(4-methoxyphenyl)propan-2-amine | HCID 40492852 | 44% |
Reaction Steps
A sample of 3.36 g (13.2 mmol) of the racemate 1-(4′-methoxyphenyl)-2-benzylaminopropane (42) was reacted with 2.0 g (13.2 mmol) of (R)-(−)-mandelic acid to give 740 mg (44% based on enantiomeric abundance) of the free amine after workup. 1H NMR, (CDCl3) δ□ 1.10 (d, 3H, J=6.2 Hz), 2.55-2.76 (m, 2H), 2.88-2.95 (m, 1H), 3.73-3.88 (m, 2H), 3.79 (s, 3H), 6.80 (d, 2H, J=8.7 Hz), 7.08 (d, 2H, J=8.4 Hz), 7.15-7.30 (m, 5H); MS (APCI+) m/z (rel): 256 (100); [α]D=+30.5° (c=1.1 MeOH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08703826B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-e503b5db6f944bafad255d4e83a93a28 |
| Source note | uspto-grants-2014_04 |