(+)-1-(1-Naphthyl)ethylamine → 1-(1-Naphthyl)ethylamine
Reaction equation
[C:1]1([C@H:11]([NH2:13])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C1C=C(C=CC=O)C=CC=1>CO>[C:1]1([CH:11]([NH2:13])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
23.1 Kg of (R)-(+)-1-(1-naphthyl)ethylamine, 150.2 Kg of methyl alcohol, 27.7 Kg of 3-[3-(trifluoromethyl)phenyl]propenaldehyde were loaded in a reactor. The mass was stirred at a temperature of 20-30° C. for a few hours, thereby obtaining the non isolated intermediate (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino-N-[1-(1-naphthyl)ethylamine (IV) in a methanol solution. The intermediate was reduced by pouring a solution of 3.9 Kg of sodium borohydride dissolved in 46.2 Kg of methanol and 0.6 of 30% sodium hydrate in the mass. The mass was stirred at a temperature of 0-20° C. until the Schiff base was reduced. 4.9 Kg of 80% acetic acid were then poured and methanol was distilled. 207.9 Kg of toluol and 138.6 Kg of water were added to the residue and the mass was stirred, separated and then the aqueous phase was discarded.
Sources & evidence
- ORD record
- ord-d0a7ceb208924775a94335aa4f747bb2
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614354B2
Reaction notes
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