N,1-diphenylethan-1-imine → N-(1-Phenylethyl)aniline

HRID 1014770Notes

Reaction equation

HRID 1014770 reaction equation
[C:1]1([C:7](=[N:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl>[C:1]1([CH:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 555698N,1-diphenylethan-1-imine

Product 1

HCID 418090N-(1-Phenylethyl)anilineYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of N-(1-phenylethylidene)aniline (50 mg, 0.26 mmol) and rac-32 (7.8 mg, 0.0050 mmol, 1.9 mol %) in CH2Cl2 (3 mL) was pressurized with H2 to 62 bar and stirred for 72 h. Filtration of the reaction mixture and evaporation of the solvent gave 42 as a clear oil (41 mg, 81%). 1H NMR28 (300 MHz, CDCl3): δ 7.50-7.35 (m, 4H), 7.30-7.25 (m, 1H), 7.15 (t, 2H, J=7.5 Hz), 6.70 (t, 1H, J=7.5 Hz), 6.59 (d, 2H, J=7.5 Hz), 4.56 (quin, 1H, J=6.6 Hz), 4.08 (bs, 1H), 1.56 (d, 3H, J=6.6 Hz); 13C NMR (75.5 MHz, CDCl3): δ 147.4, 145.4, 129.3, 128.8, 127.0, 126.0, 117.4, 113.4, 53.6, 25.2.

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent

Sources & evidence

ORD record
ord-635467ca111a4fd5bff8bea38825d74b
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

Loading…