Water → HCID 131721758, compound

HRID 1004146Notes

Reaction equation

HRID 1004146 reaction equation
[CH2:1]([CH2:16]/[C:17](/[CH3:36])=[CH:18]/[CH2:19][CH2:20]/[C:21](/[CH3:35])=[CH:22]/[CH2:23][CH2:24]/[C:25](/[CH3:34])=[CH:26]/[CH2:27][CH2:28]/[C:29](/[CH3:33])=[CH:30]/[CH2:31]Br)[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].[CH2:37]([NH2:47])[C:38]1[CH:46]=[CH:45][C:44]2[O:43][CH2:42][O:41][C:40]=2[CH:39]=1.O>C1COCC1>[CH2:1]([CH2:16]/[C:17](/[CH3:36])=[CH:18]/[CH2:19][CH2:20]/[C:21](/[CH3:35])=[CH:22]/[CH2:23][CH2:24]/[C:25](/[CH3:34])=[CH:26]/[CH2:27][CH2:28]/[C:29](/[CH3:33])=[CH:30]/[CH2:31][NH:47][CH2:37][C:38]1[CH:46]=[CH:45][C:44]2[O:43][CH2:42][O:41][C:40]=2[CH:39]=1)[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 131721759HCID 131721759, compound

Product 1

HCID 131721758HCID 131721758, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of THF was dissolved 4.56 g of farnesylgeranylgeranyl bromide, 3.01 g 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 1.14 g of N-farnesylgeranylgeranylpiperonylamine 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-6908e8b1e99f4502924eaa253e067a14
Source dataset
uspto-grants-2000_04
Patent number
US06048882

Reaction notes

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