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(+)-1-(1-Naphthyl)ethylamine → 1-(1-Naphthyl)ethylamine

HRID 1915195
Notes
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Reaction equation

HRID 1915195 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]=1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 534010893-[3-(Trifluoromethyl)phenyl]-2-propenal

Product 1

HCID 980891-(1-Naphthyl)ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08614354B2

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes