Ethylamine → N-Ethyl-4-bromobenzylamine

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][CH:3]=1.[CH2:10]([NH2:12])[CH3:11]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:12][CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6341Ethylamine

HCID 685274-Bromobenzyl bromide

Product 1

HCID 4716477N-Ethyl-4-bromobenzylamineYield 75.9%

Procedure

Following the procedure outlined for Example 488, 1-bromo-4-(bromomethyl)benzene (2.0 g, 8.0 mmol) was reacted with ethanamine (720 mg, 16 mmol) to afford the desired product (1.3 g, 75%) as a brown solid: ESI MS m/z 215 [C9H12BrN+H]+.

Sources & evidence

ORD record: ord-1a26f87c973348ab9dc589b9c4020042
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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