N-benzyl-1-phenylethanimine → N-benzyl-1-phenylethylamine

HRID 1014771Notes

Reaction equation

HRID 1014771 reaction equation
[C:1]1([CH2:7][N:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl>[CH2:7]([NH:8][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 297338N-benzyl-1-phenylethanimine

Product 1

HCID 519427N-benzyl-1-phenylethylamineYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of 1-phenyl-N-(1-phenylethylidene)methanamine (50 mg, 0.24 mmol) and rac-32 (7.5 mg, 0.0048 mmol, 2.0 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 43 as a clear oil (45 mg, 88%). 1H NMR29 (300 MHz, CDCl3): δ 7.35-7.27 (m, 10H), 3.85 (q, 1H, J=6.6 Hz), 3.66 (ABq, 2H, J=13.2 Hz), 1.59 (bs, 1H), 1.39 (d, 3H, J=6.6 Hz); 13C NMR (75.5 MHz, CDCl3): δ 145.7, 140.8, 128.6, 128.5, 128.3, 127.0, 126.95, 126.8, 57.6, 51.8, 24.7.

Workup

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

Sources & evidence

ORD record
ord-d3ea57973c5448278352ed89be8f2ba3
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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