4-Bromotoluene → HCID 9834366, compound

HRID 1883459Notes

Reaction equation

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

Participants

Reactant 2

HCID 78054-Bromotoluene

HCID 769382-(1-Cyclohexenyl)ethylamine

Product 1

HCID 9834366HCID 9834366, compoundYield 92%

Procedure

Using the general procedure, 4-bromotoluene (172 mg, 1.0 mmol) was coupled with 2-(1-cyclohexenyl)ethylamine (209 μL, 1.5 mmol) at 100° C. for 20 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (20:1) as eluent afforded the desired product as a colorless oil (198 mg, 92% yield). Rf=0.6 (hexane/ethyl acetate=10:1).

Workup

customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record: ord-f84e5f6cc2dc4de38ae9bed214aa6128
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759554B2

Reaction notes

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