Water → N-geranylgeranylpiperonylamine

HRID 1004144Notes

Reaction equation

HRID 1004144 reaction equation
[CH2:1]([CH2:11]/[C:12](/[CH3:21])=[CH:13]/[CH2:14][CH2:15]/[C:16](/[CH3:20])=[CH:17]/[CH2:18]Br)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[CH2:22]([NH2:32])[C:23]1[CH:31]=[CH:30][C:29]2[O:28][CH2:27][O:26][C:25]=2[CH:24]=1.O>C1COCC1>[CH2:1]([CH2:11]/[C:12](/[CH3:21])=[CH:13]/[CH2:14][CH2:15]/[C:16](/[CH3:20])=[CH:17]/[CH2:18][NH:32][CH2:22][C:23]1[CH:31]=[CH:30][C:29]2[O:28][CH2:27][O:26][C:25]=2[CH:24]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 11175640HCID 11175640, compound

Product 1

HCID 70192114N-geranylgeranylpiperonylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 200 ml of THF was dissolved 20.5 g of geranylgeranyl bromide, 14.4 ml of piperonylamine was added and stirred at room temperature for one hour. To the reaction mixture was added water and extracted with ethyl acetate. The extract was washed with water and then brine, dried over magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (using as a developing solvent hexane-ethyl acetate (4:1)→ethyl acetate) to give 17.6 g of N-geranylgeranylpiperonylamine as a yellow liquid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-357b2bc83ce046f08ebd007e1d2b04ec
Source dataset
uspto-grants-2000_04
Patent number
US06048882

Reaction notes

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