1-Phenethylamine → N-(1-naphthalen-1-ylethyl)-1-phenylethanamine

HRID 322598

Reaction equation

HRID 322598 reaction equation
Cl.CO[C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([NH:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH3:11])=[CH:6][CH:5]=1.C1(C(N)C)C=CC=CC=1.C(C1C2C(=CC=CC=2)C=CC=1)(=O)C.C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:15]1([CH:13]([NH:12][CH:10]([C:7]2[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=2)[CH3:11])[CH3:14])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 74081-PhenethylamineHCID 136631-AcetylnaphthaleneHCID 5003444Sodium cyanoborohydrideHCID 69657690(R)-N-(1-(4-methoxyphenyl)ethyl)-(R)-1-(1-naphthyl) ethylamine hydrochloride

Product 1

HCID 22011087N-(1-naphthalen-1-ylethyl)-1-phenylethanamine

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

In a similar fashion equal molar amounts of (R))-1-phenylethylamine, 1′-acetonaphthone and 1.25 equivalents of titanium(IV) isopropoxide were mixed and the resulting intermediate imine was reduced with ethanolic sodium cyanoborohydride. Work-up and chromatography yielded N-[1-(1-naphthyl)ethyl)-1-phenylethylamine, 4G, as a clear, colorless oil; m/z (rel. int.) 275 (M+, 16), 260 (79), 155 (100), 127 (27), 105 (70), 77 (32).

Sources & evidence

ORD record
ord-5574b43b0c1941e8afe08e58d6314ea5
Source dataset
uspto-grants-2001_04
Patent number
US06211244B1

Linked notes

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