Furfurylamine → N-(furan-2-ylmethyl)-1,3-benzodioxol-5-amine

HRID 984675Notes

Reaction equation

HRID 984675 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1.[CH2:11]([NH2:17])[C:12]1[O:16][CH:15]=[CH:14][CH:13]=1>>[CH2:9]1[O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:17][CH2:11][C:12]3[O:16][CH:15]=[CH:14][CH:13]=3)=[CH:3][C:4]=2[O:10]1

Participants

3

Reactant 2

HCID 3438FurfurylamineHCID 758311-Bromo-3,4-(methylenedioxy)benzene

Product 1

HCID 784117N-(furan-2-ylmethyl)-1,3-benzodioxol-5-amineYield 87%

Procedure

Using the general procedure, 4-bromo-1,2-(methylenedioxy)benzene (120 μL, 1.0 mmol) was coupled with furfurylamine (132 μL, 1.5 mmol). Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (8:1) as eluent afforded the desired product as a colorless oil (187 mg, 87% yield). Rf=0.5 (hexane/ethyl acetate=5:1).

Workup

  1. customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record
ord-c0ee29d1a9da4c11afc731b9ca400e9d
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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