Hexylamine → N-Hexyl-2-methoxybenzenamine

HRID 1883449Notes

Reaction equation

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

Participants

Reactant 2

HCID 8102Hexylamine

HCID 113582-Bromoanisole

Product 1

HCID 10727039N-Hexyl-2-methoxybenzenamineYield 89%

Procedure

Using the general procedure, 2-bromoanisole (125 μL, 1.0 mmol) was coupled with n-hexylamine (198 μL, 1.5 mmol) at 100° C. for 22 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (30:1) as eluent afforded the desired product as a colorless liquid (184 mg, 89% yield). Rf=0.4 (hexane/ethyl acetate=20:1).

Workup

customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record: ord-4d683567e85543b598f3860c4ec550f7
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759554B2

Reaction notes

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