4-Methoxybenzaldehyde → N-(4-Methoxybenzylidene)-N-(4-methoxybenzyl)amine

HRID 1097562Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:8]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 312444-Methoxybenzaldehyde

HCID 754524-Methoxybenzylamine

Product 1

HCID 578709N-(4-Methoxybenzylidene)-N-(4-methoxybenzyl)amineYield 131%

Procedure

4-Methoxybenzylamine (40 g, 290 mmol) was cooled to 0° C., and p-anisaldehyde (39.7 g, 292 mmol) was added dropwise. The reaction was stirred at ambient temperature for two hours, concentrated under reduced pressure, and further dried under high vacuum overnight to provide 97 g of N-(4-methoxybenzyl)-N-[(4-methoxyphenyl)methylidene]amine as a white, waxy solid.

Workup

concentrationconcentrated under reduced pressure
customfurther dried under high vacuum overnight

Sources & evidence

ORD record: ord-b566f8d0d4604980b48691a32407a87c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143270B2

Reaction notes

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