4-Methoxybenzylamine → 2-(4-Methoxybenzylamino)-6-(trifluoromethyl)benzonitrile

HRID 711754Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=1[C:4]#[N:5].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1>O1CCOCC1>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][C:2]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=2[C:4]#[N:5])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 180 °C

Procedure

2-Fluoro-6-(trifluoromethyl)benzonitrile (2.44 g, 12.9 mmol) and 4-methoxybenzylamine (7.09 g, 51.7 mmol) were suspended in 1,4-dioxane (10 mL) and heated in a microwave at 180° C. for 30 min. The 1,4-dioxane was removed under vacuum, and the crude material was purified by chromatography on silica gel eluting with CH2Cl2 to give 3.71 g of 2-(4-methoxybenzylamino)-6-(trifluoromethyl)benzonitrile (94%) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ 3.71 (s, 3H), 4.42 (d, J=5.6 Hz, 2H), 6.89 (m, 2H), 6.97 (m, 2H), 7.29 (m, 3H), 7.48 (m, 1H).

Workup

customThe 1,4-dioxane was removed under vacuum
customthe crude material was purified by chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record: ord-fc5aacea3b554eb594eaaa97fdf483bc
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Reaction notes

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