Benzaldehyde → N-[2-(diphenylphosphino)ethyl]-N-[phenylmethylene]amine

HRID 2364112

Reaction equation

HRID 2364112 reaction equation
[C:1]1([P:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:1]1([P:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][N:10]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 273264(2-Aminoethyl)diphenylphosphine

Product 1

HCID 12145947N-[2-(diphenylphosphino)ethyl]-N-[phenylmethylene]amineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon, a solution of 2-diphenylphosphino-ethylamine (590.3 mg, 2.57 mmol) and benzaldehyde (275.0 mg, 2.59 mmol) in ethanol (15 mL) was heated at 65° C. (oil bath) for 4 h. Then, the solvent was removed in-vacuo to give the desired product (>98% by 1H-NMR) as a colourless oil which solidified on standing (733.9 mg, 2.31 mmol, 90%).

Workup

  1. customThen, the solvent was removed in-vacuo

Sources & evidence

ORD record
ord-bce3ded93bba4133909b30d08d25708c
Source dataset
uspto-grants-2014_04
Patent number
US08692022B2

Linked notes

Loading…